Name: 1137-41-3|(4-Aminophenyl)(phenyl)methanone|95%
Brand: Ambeed
SKU: A355876
Rating: 91 (32 reviews)

1
[ 1144-74-7 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; triruthenium dodecacarbonyl; 2-methoxy-ethanol; carbon monoxide; benzyl-triethyl-ammonium chloride In benzene for 4.5h; Ambient temperature;
99%	With TPGS-750-M; ammonia hydrochloride; zinc In lithium hydroxide monohydrate at 20℃; for 4h; Green chemistry; chemoselective reaction;
98%	With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 20℃; for 4h; Green chemistry;	4.5 General procedure for the reduction of nitro aromatic using starch-crt(at)Au General procedure: To a flask containing nitroarene (0.5 mmol), starch-crt(at)Au (0.1 mol%, 25 mg) and NaBH4 (2.5 mmol, 45 mg), 2 mL of H2O:EtOH (1:1) was added. Reaction mixture was stirred at room temperature for the appropriate reaction times (see Tables 2 and 3). Progress of the reactions were monitored by GC, TLC and or 1H NMR. After completion of the reaction, the crude product was extracted with ethyl acetate (3 × 5 mL). The solvent was evaporated and the residue was purified using column or plate chromatography.

97%	With sodium tetrahydridoborate; NiCl₂·6H₂O In lithium hydroxide monohydrate at 20℃; for 3h; Inert atmosphere; Green chemistry;
96%	With trichlorosilane; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 0.0833333h; Flow reactor;	General procedure for the continuous-flow reaction using a0.5 mL PTFE reactor General procedure: Syringe A was filled with a solution ofHSiCl3 (2.4 mmol) in dry CH2Cl2 (1.5 mL). Syringe B wasloaded with a solution of the nitro compound (0.6 mmol) andHünig’s base (3.6 mmol) in dry CH2Cl2 (1.5 mL). Syringes Aand B were connected to a syringe pump and the reagents werepumped into the microreactor at the indicated flow rate(mL/min) at room temperature. The outcome of the reactor wascollected in a flask containing a 10% NaOH solution. Fivereactor volumes were collected. CH2Cl2 was removed in vacuoand the aqueous layer was extracted three times with ethylacetate. The combined organic layers were washed with brine,dried with Na2SO4 and concentrated in vacuo. 1H NMR spectroscopy of the crude was used to calculate the reaction conversion; in case of a full conversion of the starting material nofurther purification was required
95%	Stage #1: (4-nitrophenyl)(phenyl)methanone With hydrogen bromide; hypophosphorous acid; glacial acetic acid; sodium iodide In lithium hydroxide monohydrate at 115℃; for 3h; Inert atmosphere; Stage #2: With sodium hydroxide In lithium hydroxide monohydrate Inert atmosphere;
95%	Stage #1: (4-nitrophenyl)(phenyl)methanone With N-phenylhydrazine monohydrochloride at 65℃; Stage #2: With 5-aminotetrazole Reflux;	8 synthesis of p-aminobenzophenone A ketoprofen intermediate for the synthesis of p-aminobenzophenone, comprising the steps of:A, in a reaction vessel equipped with a stirrer, a reflux condenser, and a dropping funnel, 700 ml of a phenylhydrazine hydrochloride solution, 0.61 mol of p-nitrobenzophenone was added and the stirring speed was controlled at 170 rpm, Temperature to 65 , reflux 3h;B, dropping 43% 5-aminotetrazole solution 300ml, dropping time control in 3h, after adding the continued reflux 90min, 3.3kPa vacuum distillation 2h;C, reduce the temperature of the solution to 10 , filter, ammonium nitrate solution, add it to 1.5L mass fraction of 33% oxalic acid solution, raise the temperature of the solution to 70 , keep 60min, filter, add the filtrate 300ml mass fraction 27% potassium sulfite solution, precipitation of solid, reduce the temperature of the solution to 20 , filtration, the mass fraction of 15% sodium bromide solution washing, anhydrous calcium chloride dehydration agent dehydration, p-amino benzophenone 113.56g, yield 94%. The mass fraction of the sulfite solution in Example 1 is adjusted to the same as the remaining ratio of raw materials and preparation conditions in Example to obtain a reaction yield Seen from Example 8, the yield of the reaction mass is proportional to the fraction of the solution with sulfite, potassium sulfite solution, the mass fraction of low yield great influence on the reaction, considering the cost, the sulfite solution is preferably a mass fraction of 25-29%.
95%	With hydrogen In 2-methyltetrahydrofuran; lithium hydroxide monohydrate at 40℃; for 24h; chemoselective reaction;
93%	With 2,3-dimethyl-2,3-butane diol; MoO<SUB>2</SUB>Cl<SUB>2</SUB>(DMF)<SUB>2</SUB> In toluene at 150℃; for 0.333333h; Microwave irradiation; chemoselective reaction;
93%	With trichlorosilane; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 18h; Inert atmosphere; chemoselective reaction;
93%	Stage #1: (4-nitrophenyl)(phenyl)methanone With hydrogenchloride; 1,1,1,3',3',3'-hexafluoro-propanol; iron⁽⁰⁾ In lithium hydroxide monohydrate at 20℃; for 0.5h; Stage #2: With Sodium hydrogenocarbonate In lithium hydroxide monohydrate chemoselective reaction;	2. General Procedure for the Reduction of Nitro Compounds General procedure: The nitro compound (1 equiv), HFIP (10 equiv), Fe powder (5 equiv) were mixed in a tube. Then 2 N HCl aqueous solutions was added to the reaction mixture. After stirring at room temperature for 30 min, the reaction mixture was neutralized with sat. NaHCO3 (aq.) and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was then purified by column chromatography on silica gel to furnish the desired amine product.
92%	With anhydrous ammonium formate; zinc In methanol at 20℃; for 0.166667h;
92%	With hydrogen In ethanol at 60℃; for 10h;	13 Preparation of 4-aminobenzophenone Nano-porous metal cesium catalyst (3.2 mg, 0.03 mmol) Ethanol (lmL) and 4-nitrobenzophenone (68.17mg, 0.3mmol) were added to the reaction kettle, hydrogen (10 bar) was added, heated and stirred, the reaction temperature was controlled at 60 ° C, The reaction time was controlled at 10 h, column chromatography (baby gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate = 10: 1) to give 54.4 mg of 4-aminobenzophenone in 92% yield.
92%	With hydrogen In toluene at 140℃; for 48h; chemoselective reaction;
91%	With sodium hydroxide; carbon monoxide In lithium hydroxide monohydrate; toluene at 30℃; for 1.08333h; specific rate of reduction under biphasic condition;
91%	With iron⁽⁰⁾; glacial acetic acid In ethanol for 2h; Heating;
91%	With triethylamine In lithium hydroxide monohydrate at 80℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;
90%	With potassium hydroxide; isopropanol for 3h; Heating;
90%	With formic acid; nickel In methanol at 20℃; for 0.333333h;
90%	With formic acid at 140℃; for 0.133333h; Microwave irradiation;
89%	With nickel oxide; aluminum(III) oxide; potassium hydroxide; isopropanol In nitrobenzene for 1h; Heating;
89%	With potassium hydroxide; isopropanol for 1h; Heating;
89%	With sodium tetrahydridoborate; lithium hydroxide monohydrate at 20℃; for 1h;	2.3. Heterogeneous reduction of nitroarenes catalyzed by the CoFe₂O₄Pd/AC nanocomposite Reduction of nitroarenes was carried out in a 10 mL round-bottomflask equipped with a magnetic stirrer. First, 6 mg of the CoFe2O4Pd/AC was dispersed in 3 mL deionized water. Then, 1 mmol of the nitroarenewas added to the flask. With a continuous stirring at room temperature,1.5 mmol of NaBH4 in 4 mL deionized water was slowly addedto the reaction vessel during stirring. After appropriate time, thecompletion of the reaction was monitored by thin-layer chromatography(TLC). The catalyst was separated by using an external magnet from thereaction mixture. The mixture was decanted and extracted by ethyl acetateand dried over anhydrous Mg2SO4. The isolated product was obtainedby evaporating the ethyl acetate and subjected to characterizationby IR spectroscopy.
85%	With sodium hydroxide; baker's yeast In methanol; lithium hydroxide monohydrate at 70 - 80℃; for 5h;
84%	With stainless steel; lithium hydroxide monohydrate; chromium; zirconium oxide for 3h;	9 Example 9 Synthesis of 4-Aminobenzophenone Through Hydrogenation Reaction of 4-Nitrobenzophenone Example 9 Synthesis of 4-Aminobenzophenone Through Hydrogenation Reaction of 4-Nitrobenzophenone [0112] 91.1 mg (0.50 mmol) of 4-nitrobenzophenone (7) and 270 μL (15 mmol) of distilled water were placed in a planetary ball mill vessel (12 mL), in which 50 pieces of balls made of zirconia (diameter: 5 to 6 mm) and 78 mg (1.5 mmol) of chromium powder were placed, and the equipment was then closed and rotated for 3 hours at 800 rpm (reversed every 30 minutes) for agitation. After a lapse of 3 hours, 10 mL of ethyl acetate was added to the planetary ball mill vessel to provide a solution containing the reaction mixture, which was then filtered with Celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, and then 1H NMR confirmed that 4-aminobenzophenone (8) was obtained. The yield was 84%. The reaction is expressed by the following scheme.
83%	With tetrahydroxydiborane; 5%-palladium/activated carbon; lithium hydroxide monohydrate In acetonitrile at 50℃; for 24h; chemoselective reaction;	4.2 Typical procedure for reduction of nitrobenzene General procedure: Nitrobenzene (0.6mmol), 5wt% Pd/C (0.5mmol %, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50°C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99%).
82%	With sodium tetrahydridoborate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 4h; Inert atmosphere; Green chemistry; chemoselective reaction;
81%	With tetrahydroxydiborane; palladium on activated charcoal; lithium hydroxide monohydrate In acetonitrile at 50℃; for 24h; Inert atmosphere;	16; 41; 52 Example 16Synthesis of 4-aminobenzophenone 4-nitrobenzophenone (0.6mmol, 99.1mg), water (6mmol, 108.0mg), Pd/C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.98mmol, 177.5mg), acetonitrile (1mL ), under the protection of nitrogen, react at 50C for 24h, monitor the reaction by TLC, add 10mL water, extract with ethyl acetate (10mL×3), combine the organic phases, dry with anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (V Petroleum ether: V ethyl acetate = 3:1) to obtain 95.9 mg of a yellow solid, that is, to obtain the target compound with a yield of 81%.
72%	With titanium(IV) tetrachloride; diisobutyl telluride In dichloromethane for 0.5h; Ambient temperature;
72%	With Zr₁₂(μ₃-O)₅[(μ₃-O)CoCl]₈[(μ₂-O)₂(μ₃-O)CoCl]₃Li₃(triphenyldicarboxylate)₉; hydrogen; sodium triethylborohydride In toluene at 110℃; for 42h; Inert atmosphere; Schlenk technique;
71%	With aluminum(III) oxide; dicobalt octacarbonyl In hexane
71%	With tetrahydroxydiborane; copper (II) acetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction;	4.1.2. Typical procedure for the synthesis of 8-Aminoquinoline (4a) General procedure: A 20 mL Schlenk tube was charged with 8-nitroquinoline (1k; 87 mg, 0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4(135 mg, 1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 80 °C for 24 h, then cooled to room temperature and concentrated under reduced pressure. Similar workup to 2a gave a brown solid (4a: 63 mg, 87% yield).
63%	With iron sulphate heptahydrate; Aluminum Chloride; zinc In ethanol; lithium hydroxide monohydrate at 50℃; for 2h;
	With hydrogenchloride; ethanol; stannous chloride
	With 1,4-dioxane; platinum Hydrogenation;
	With ethanol; nickel Hydrogenation;
	With tin; glacial acetic acid
	With reducing agent
	With hydrogenchloride; iron⁽⁰⁾; ammonia hydrochloride In ethanol at 55 - 65℃;
100 %Chromat.	With titanium dioxide In ethanol for 1.25h; Irradiation; Green chemistry; chemoselective reaction;	Photocatalytic synthesis of aromatic amines General procedure: Photocatalytic synthesis of aromatic amines. Photocatalytic reactions were carried out in a round bottomed Pyrex flask and irradiated using four high power blue light LEDs 3W lamp or by solar light under magnetic stirring at room temperature. Reaction conditions with solar light: the reduction of the aromatic nitro compounds (0.02 mmol) was carried out in the presence of TiO2-P25 (0.01 g) in EtOH (4 mL) with irradiation for 1-4 h.
100 %Chromat.	With oxalic acid; titanium(IV) dioxide; β‐cyclodextrin In lithium hydroxide monohydrate for 2h; Inert atmosphere; Irradiation; Green chemistry;
93 %Chromat.	With cadmium sulphide In isopropanol for 1.16667h; Inert atmosphere; Sonication; Irradiation;	Experimental General procedure: As optimized reaction conditions, a solution of nitroaromaticcompounds (0.01 M) in an appropriatesolvent and 20 mg of CdS-NP were sonicated andslowly purged with N2 for 5 min. Then, the reactionvessel was sealed up with a rubber stopper and themixture was stirred magnetically and irradiated with blue LED (4 × 1 W, λ ≥ 420 nm, intensity: 80 lumen)or sunlight (of daily ambient temperature andsunlight intensity range of 80-100 × 103 lux).The reaction conversion was monitored by thinlayer chromatography (TLC). After completing thereaction, the mixture was centrifuged and supernatantwas removed and analyzed on a GC Alientgas chromatograph (Nonpolar CP-Sil 8 column (30m × 0.32 mm), Varian Chrompack (Middelburg, TheNetherlands).
	With ammonia; hydrogen In methanol at 90℃; for 38h; Autoclave;
93 %Chromat.	With hydrogen; triethylamine In ethanol; lithium hydroxide monohydrate at 110℃; for 22h; Autoclave; chemoselective reaction;
95 %Chromat.	With cadmium sulfide loaded on silica-coated Fe₃O₄ nanoparticles In isopropanol for 20h; Irradiation; Inert atmosphere;	2.3 Photocatalytic activity General procedure: The Fe3O4/SiO2/CdS (S2) with average amount of CdS has been chosen as a photocatalyst for the photocatalytic reduction of nitro compounds under the blue LED irradiation. In a 10mL flask, 5ml of 0.01M nitro compounds solution and 0.02g photocatalyst were charged. Then the flask was charged with pure argon. The resulting mixture was stirred for 20h under LED irradiation. After this time, the catalyst was simply separated by employing an external magnetic field and the remaining solution was analyzed using thin-layered chromatography (TLC) and Varian gas chromatograph (CP-3800). The conversion of nitro substrate, yield of amine, and selectivity for amine were defined as follows: Conversion (%) = (C0-Cnitro)/C0×100 Yield (%) = Camine/C0×100 Selectivity (%) =Camine/(C0-Cnitro)×100Where C0 is the initial concentration of nitro compound and Cnitro and Camine are the concentration of the nitro substrate and the corresponding amine respectively, after the photocatalytic reaction.
93 %Chromat.	With hydrogen; triethylamine In ethanol; lithium hydroxide monohydrate at 110℃; for 22h; Autoclave;	3.1.1; 3.1.9 General Procedure for the Preparation of substituted Anilines from Nitroarenes General procedure: In a 4 ml_ reaction glass vial fitted with a septum cap containing a magnetic stirring bar, Co-Co3O4Chit-700 (10 mg, 3.4 mol% Co), the nitroarenes (0.5 mmol, 1 .0 equiv.) and triethylamine (35 μΙ_, 0.25 mmol, 0.5 equiv.) were added to a solvent mixture of EtOH/H20 (3/1 , 2 ml_). The reaction vial was then placed into a 300 ml_ autoclave, flashed with hydrogen five times and finally pressurized to 40 bar. The reaction mixture was stirred for appropriate time at 1 10 °C. After cooling the reaction mixture to room temperature, the autoclave was slowly depressurized. The crude reaction mixture was filtered through a pipette fitted with a cotton bed and the solvent was evaporated under reduced pressure. The crude products were purified by passing through a silica plug (eluent: ethyl acetate) to give pure aniline derivatives after removal of solvent. The following compounds may be prepared from the respective nitroarenes using the catalyst of the invention:
> 99 %Chromat.	With tris(2,2′-bipyridine)ruthenium(II) hexafluorophosphate; 3C₉₃H₇₂N₈O₄P₄^(4-)*6Co⁽²⁺⁾; quinhydrone; L-ascorbic acid In lithium hydroxide monohydrate; acetonitrile at 24.84℃; for 12h; Inert atmosphere; Irradiation;	4.3 General procedure for selective hydrogenation of nitroarenes to anilines General procedure: In a typical experiment, selective hydrogenation of nitroarenes to anilines was made in a 20mL flask. Varying amounts of the p-nitroacetophenone, the catalyst, Ru(bpy)32+ and ascorbic acid in 1:1 CH3CN/H2O were added to obtain a total volume of 5.0mL. The flask was sealed with a septum, degassed by bubbling argon for 15min under atmospheric pressure at room temperature. The pH of this solution was adjusted to a specific pH by adding H2SO4 or NaOH and measured with a pH meter. After that, the samples were irradiated by a 500W Xenon Lamp, the reaction temperature was 298K by using a water filter to absorb heat. The generated photoproduct of selective hydrogenation of nitroarenes evolution was characterized by GC-MS analysis.
	With hydrogen In methanol; lithium hydroxide monohydrate at 90℃; for 5h;
90 %Chromat.	With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 20℃; for 1.5h;

Reference： [1]Alper, Howard; Amaratunga, Shiyamalie [Tetrahedron Letters, 1980, vol. 21, # 27, p. 2603 - 2604]
[2]Kelly, Sean M.; Lipshutz, Bruce H. [Organic Letters, 2014, vol. 16, # 1, p. 98 - 101]
[3]Gholinejad, Mohammad; Dasvarz, Neda; Shojafar, Mohammad; Sansano, José M. [Inorganica Chimica Acta, 2019, vol. 495]
[4]Prathap, Kaniraj Jeya; Wu, Qiong; Olsson, Richard T.; Dinér, Peter [Organic Letters, 2017, vol. 19, # 18, p. 4746 - 4749]
[5]Porta, Riccardo; Puglisi, Alessandra; Colombo, Giacomo; Rossi, Sergio; Benaglia, Maurizio [Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2614 - 2619]
[6]Wu, George G.; Chen, Frank X.; LaFrance, Danny; Liu, Zhijian; Greene, Scott G.; Wong, Yee-Shing; Xie, Ji [Organic Letters, 2011, vol. 13, # 19, p. 5220 - 5223]
[7]Current Patent Assignee: CHENGDU DONGDIAN AIER TECH - CN106083620, 2016, A Location in patent: Paragraph 0017; 0018; 0023-0027; 0062-0065
[8]Li, Wu; Artz, Jens; Broicher, Cornelia; Junge, Kathrin; Hartmann, Heinrich; Besmehn, Astrid; Palkovits, Regina; Beller, Matthias [Catalysis science and technology, 2019, vol. 9, # 1, p. 157 - 162]
[9]Garcia, Nuria; Garcia-Garcia, Patricia; Fernandez-Rodriguez, Manuel A.; Rubio, Ruben; Pedrosa, Maria R.; Arnaiz, Francisco J.; Sanz, Roberto [Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 321 - 327]
[10]Orlandi; Tosi; Bonsignore; Benaglia [Organic Letters, 2015, vol. 17, # 16, p. 3941 - 3943]
[11]Chen, Xu-Ling; Ai, Bai-Ru; Dong, Yu; Zhang, Xiao-Mei; Wang, Ji-Yu [Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649]
[12]Gowda, D. Channe; Mahesh, B.; Gowda, Shankare [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 1, p. 75 - 77]
[13]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN107098786, 2017, A Location in patent: Paragraph 0058-0059
[14]Li, Wu; Cui, Xinjiang; Junge, Kathrin; Surkus, Annette-Enrica; Kreyenschulte, Carsten; Bartling, Stephan; Beller, Matthias [ACS Catalysis, 2019, p. 4302 - 4307]
[15]Joo, Ferenc; Alper, Howard [Canadian Journal of Chemistry, 1985, vol. 63, p. 1157 - 1160]
[16]Davies; Nagashima; Klino 3rd. [Organic letters, 2000, vol. 2, # 6, p. 823 - 826]
[17]Damodara, Dandu; Arundhathi, Racha; Ramesh Babu, T. Venkata; Legan, Margaret K.; Kumpaty, Hephzibah J.; Likhar, Pravin R. [RSC Advances, 2014, vol. 4, # 43, p. 22567 - 22574]
[18]Upadhya; Katdare; Sabde; Ramaswamy, Veda; Sudalai [Chemical Communications, 1997, # 12, p. 1119 - 1120]
[19]Channe Gowda; Prakasha Gowda; Ramesha Baba; Gowda, Shankare [Synthetic Communications, 2000, vol. 30, # 16, p. 2889 - 2895]
[20]Location in patent: experimental part Arya, Kapil; Dandia, Anshu [Journal of the Korean Chemical Society, 2010, vol. 54, # 1, p. 55 - 58]
[21]Jyothi; Raja; Talawar; Sreekumar; Sugunan; Rao [Synthetic Communications, 2000, vol. 30, # 9, p. 1573 - 1579]
[22]Jyothi; Talawar; Raja; Sreekumar; Rajagopal; Rao [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 6, p. 1425 - 1427]
[23]Hamadi, Hosein; Kazeminezhad, Iraj; Mohammadian, Sara [Journal of Solid State Chemistry, 2021, vol. 302]
[24]Baik, Woonphil; Han, Jeong Lim; Lee, Ki Chang; Lee, Nam Ho; Kini, Byeong Hyo; Hahn, Jung-Tai [Tetrahedron Letters, 1994, vol. 35, # 23, p. 3965 - 3966]
[25]Current Patent Assignee: SHIONO CHEMICAL - US2015/25264, 2015, A1 Location in patent: Paragraph 0112
[26]Zhou, Yanmei; Zhou, Haifeng; Liu, Sensheng; Pi, Danwei; Shen, Guanshuo [Tetrahedron, 2017, vol. 73, # 27-28, p. 3898 - 3904]
[27]Feng, Jie; Handa, Sachin; Gallou, Fabrice; Lipshutz, Bruce H. [Angewandte Chemie - International Edition, 2016, vol. 55, # 31, p. 8979 - 8983][Angew. Chem., 2016, vol. 128, # 31, p. 9125 - 9129]
[28]Current Patent Assignee: YICHANG SHANGNUODE BIOLOGY MEDICINE TECH; CHINA THREE GORGES UNIVERSITY - CN106800493, 2020, B Location in patent: Paragraph 0121-0124; 0221-0224; 0265-0268
[29]Suzuki, Hitomi; Hanazaki, Yasuaki [Chemistry Letters, 1986, p. 549 - 550]
[30]Ji, Pengfei; Manna, Kuntal; Lin, Zekai; Feng, Xuanyu; Urban, Ania; Song, Yang; Lin, Wenbin [Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 7004 - 7011]
[31]Alper, Howard; Gopal, Madhuban [Journal of Organometallic Chemistry, 1981, vol. 219, # 1, p. 125 - 127]
[32]Pi, Danwei; Zhou, Haifeng; Zhou, Yanmei; Liu, Qixing; He, Renke; Shen, Guanshuo; Uozumi, Yasuhiro [Tetrahedron, 2018, vol. 74, # 17, p. 2121 - 2129]
[33]Location in patent: experimental part Richter, Stephanie; Gioffreda, Barbara [Archiv der Pharmazie, 2011, vol. 344, # 12, p. 810 - 820]
[34]Montagne [Recueil des Travaux Chimiques des Pays-Bas, 1923, vol. 42, p. 508]
[35]Theilacker; Mueller v. Blumencron [Chemische Berichte, 1956, vol. 89, p. 984]
[36]Feldman; Sizer [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 447][Chem.Abstr., 1953, # 3315]
[37]Baeyer; Loehr [Chemische Berichte, 1890, vol. 23, p. 1623] Baeyer; Villiger [Chemische Berichte, 1904, vol. 37, p. 605]
[38]Nakata, Hisao; Tanaka, Katsunori [Organic Mass Spectrometry, 1994, vol. 29, # 6, p. 283 - 288]
[39]Liu, Yugang; Lu, Yansong; Prashad, Mahavir; Repic, Oljan; Blacklock, Thomas J. [Advanced Synthesis and Catalysis, 2005, vol. 347, # 2-3, p. 217 - 219]
[40]Zand, Zahra; Kazemi, Foad; Hosseini, Saber [Tetrahedron Letters, 2014, vol. 55, # 2, p. 338 - 341]
[41]Kakroudi, Mazaher Abdollahi; Kazemi, Foad; Kaboudin, Babak [RSC Advances, 2014, vol. 4, # 95, p. 52762 - 52769]
[42]Asghar Safari, Ali; Kazemi, Foad [Chemical Papers, 2016, vol. 70, # 5, p. 531 - 537]
[43]Formenti, Dario; Topf, Christoph; Junge, Kathrin; Ragaini, Fabio; Beller, Matthias [Catalysis science and technology, 2016, vol. 6, # 12, p. 4473 - 4477]
[44]Sahoo, Basudev; Formenti, Dario; Topf, Christoph; Bachmann, Stephan; Scalone, Michelangelo; Junge, Kathrin; Beller, Matthias [ChemSusChem, 2017, vol. 10, # 15, p. 3035 - 3039]
[45]Eskandari, Parvin; Kazemi, Foad [Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 364, p. 233 - 239]
[46]Current Patent Assignee: ROCHE HOLDING AG - WO2018/114777, 2018, A1 Location in patent: Page/Page column 31-32; 34
[47]Zheng, Sijia; Zhao, Liang; Wei, Jianwei; He, Cheng; Liu, Guangzhou; Duan, Chunying [Inorganic Chemistry Communications, 2019, vol. 109]
[48]Liu, You-Nian; Tang, Feiying; Wang, Liqiang; Wang, Xin; Zhang, Guangji [ACS Catalysis, 2022, p. 5786 - 5794]
[49]Khosravi, Faezeh; Gholinejad, Mohammad; Sansano, José M.; Luque, Rafael [Applied Organometallic Chemistry, 2022, vol. 36, # 7]

2
[ 1137-41-3 ]
[ 90-02-8 ]
[ 16678-73-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With toluene-4-sulfonic acid In ethanol for 1h; Reflux;	2.2.1 BPH. BPNH2 (1.97 g, 10 mmol) and catalytic amount of TsOH(10 mg) were added to 40 mL ethanol. The mixture was heated to reflux to get fully clear solution. Then, 10 mL ethanol solution of SA (1.22 g, 10mmol) was added dropwise to the reaction system, followed by heating the mixture at reflux for 1 h. After cooling down, the precipitate was filtered off and washed with cold ethanol (20 mL) and dried under vacuum. After recrystallization from ethanol, BPH was obtained as yellow crystal. Yiled: 76%. Mp: ca. 130 °C . 1H NMR (400 MHz,DMSO-d6) δ 12.68 (s, 1H), 9.04 (s, 1H), 7.85 (d, J = 8.4 Hz, 2H), 7.80 -7.65 (m, 4H), 7.58 (dd, J = 14.9, 8.0 Hz, 4H), 7.51 - 7.40 (m, 1H), 7.01(t, J = 8.1 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 195.73, 164.23,161.32, 152.10, 137.68, 135.73, 133.93, 132.74, 132.46, 131.71,129.95, 128.38, 121.13, 119.36, 119.00, 117.44. FT-IR (KBr): 3360(-OH), 3053 (Ar-H), 1642 (-C = O), 1620 (-C = N). HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C20H15NO2H 302.1103; found: 302.1190.
	With ethanol

Reference： [1]Li, Chao; Li, Yang; Nie, Jun; Si, Zhihao; Xue, Tanlong; Zhu, Xiaoqun [Journal of Photochemistry and Photobiology A: Chemistry, 2022, vol. 424]
[2]Torrey; Porter [Journal of the American Chemical Society, 1911, vol. 33, p. 58]

3
[ 1137-41-3 ]
[ 98-88-4 ]
[ 19617-84-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine In dichloromethane at 20℃; for 3h;
79%	With triethylamine In dichloromethane for 16h; Schlenk technique; Inert atmosphere;
	With triethylamine In benzene for 3h; Heating;

With triethylamine In dichloromethane for 4h;

Reference： [1]Dannhardt, Gerd; Fiebich, Bernd L; Schweppenhaeuser, Johannes [European Journal of Medicinal Chemistry, 2002, vol. 37, # 2, p. 147 - 161]
[2]O'Broin, Calvin Q.; Guiry, Patrick J. [Organic Letters, 2020, vol. 22, # 3, p. 879 - 883]
[3]Doebner [Justus Liebigs Annalen der Chemie, 1881, vol. 210, p. 267]
[4]Massolini, G.; Carmellino, M. L.; Baruffini, A. [Farmaco, Edizione Scientifica, 1988, vol. 43, # 6, p. 507 - 516]
[5]Schneider, Tanya L.; Halloran, Kevin T.; Hillner, Julie A.; Conry, Rebecca R.; Linton, Brian R. [Chemistry - A European Journal, 2013, vol. 19, # 45, p. 15101 - 15104]

4
[ 1137-41-3 ]
[ 708-06-5 ]
[ 16678-74-3 ]

Yield	Reaction Conditions	Operation in experiment
39.9%	In methanol at 20℃; for 6h;	Synthesis of sensor 1 10mL of methanol was used to dissolve 4-aminobenzophenone (1 mmol, 0.201g). Then, 2-hydroxy-1-naphthaldehyde (1.2mmol, 0.211g) was added slowly to the solution with stirring for 6h. The yellow product was filtered, which was washed with cold ethanol and ether. 0.140g of compound 1 was obtained (39.9%). MP (melting point): 102-106°C. 1H NMR (DMSO-d6, ppm): δ 15.55 (d, J=5.2Hz, 1H), 9.72 (d, J=5.2Hz, 1H), 8.54 (d, J=8.4Hz, 1H), 7.98 (d, J=9.6Hz, 1H), 7.88 (d, J=8.4Hz, 2H), 7.82 (m, 5H), 7.71 (t, J=7.2Hz, 1H), 7.62 (m, 3H), 7.38 (t, J=7.6Hz, 1H), 7.01 (d, J=9.2Hz, 1H); 13C NMR (DMSO-d6, ppm): δ 195.14, 172.55, 156.13, 147.75, 138.36, 137.70, 134.69, 133.60, 133.01, 131.89, 129.92, 129.54, 129.03, 128.78, 127.18, 124.27, 122.91, 120.98, 120.74, 109.30. ESI-MS m/z (1-H+): calcd, 350.12; found, 350.26. Anal. Calc. for C24H17NO2: C, 82.03; H, 4.88; N, 3.99. Found: C, 81.47; H, 4.76; N, 3.84
	With ethanol

Reference： [1]Yun, Dongju; Jung, Jae Min; Kim, Cheal [Inorganica Chimica Acta, 2018, vol. 479, p. 154 - 160]
[2]Torrey; Porter [Journal of the American Chemical Society, 1911, vol. 33, p. 58]

5
[ 1137-41-3 ]
[ 1135-12-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	With aluminum (III) chloride; lithium aluminium tetrahydride; In diethyl ether; at 0 - 20℃; for 3h;	To a mixture of LiAlH4 (10.0 equiv) in Et2O (5ml/mmol) was added the solution of AlCl3 (10.0 equiv) in Et2O (10ml/mmol) slowly at 0C, and the reaction mixture was stirred for 5min. Then the solution of (4-aminophenyl)(phenyl)methanone (12h, 1.0 equiv) in Et2O (15ml/mmol) was added, and the mixture was stirred at room temperature for 3h. After completion (monitored by TLC), the mixture was diluted using 6M HCl and neutralized by saturated sodium bicarbonate solution. Next, the solution was partitioned between water and ethyl acetate (3×). The organic layer was dried over magnesium sulfate anhydrous, filtered and concentrated in vacuo. The solid was purified by column chromatography to give the key intermediate 12f in 68% yield (Scheme S1).
	With aluminum (III) chloride; lithium aluminium tetrahydride; In diethyl ether; at 0 - 20℃; for 3h;	After LiAlH4 (10mmol, 379.5mg) was added to the reaction flask, placed after about 15min at 0 C AlCl3 (10 mmol, 1333 mg) in ether (15 ml) was added dropwise to the reaction and the mixture was stirred at 0 C for 5 min. A solution of p-aminobenzophenone (5a, 1 mmol, 197.2 mg) in ether (15 ml) was added dropwise to the reaction and the reaction was allowed to proceed to room temperature for 3 h. After completion of the reaction by TLC, the reaction solution was washed with 6 M HCl After dilution, the residue was neutralized with saturated NaHCO3 and the aqueous layer was extracted with ethyl acetate (20 ml X). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give intermediate 5b.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 134,p. 230 - 241
[2]Journal of the American Chemical Society,1950,vol. 72,p. 3586
[3]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2685 - 2688
[4]Patent: CN106496132,2017,A .Location in patent: Paragraph 0102; 0103

6
[ 1137-41-3 ]
[ 25782-57-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium tetrahydroborate In methanol at 20℃; for 1h;
95%	With methanol; sodium tetrahydroborate at 0 - 20℃;
80%	With methanol; sodium tetrahydroborate at 20℃; for 24h;	1; S3 Synthesis of compound 5 4-Aminobenzophenone (5mmol, 985 mg) was dissolved in dry methanol (50 mL), followed by addition of NaBH4(10 mmol, 378 mg). The mixture was stirred at room temperature for 24 h. After removal of the solvent, the crude product was purified by silica gel column chromatography using hexane/ethyl acetate (6/1 to 3/1) as the eluent. Compound 5 was obtained as a light yellow solid (80% yield). LRMS (ESI) m/z: calculated for C+13H14NO [M + H] 200.1, found 200.1.

73%	With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 3h;	4.3.3 N-(4-benzylphenyl)-2-((4,6-dimethylpyrimidin-2-yl)thio)acetamide (14f) To a mixture of LiAlH4 (10.0 equiv) in Et2O (5ml/mmol) was added the solution of AlCl3 (10.0 equiv) in Et2O (10ml/mmol) slowly at 0°C, and the reaction mixture was stirred for 5min. Then the solution of (4-aminophenyl)(phenyl)methanone (12h, 1.0 equiv) in Et2O (15ml/mmol) was added, and the mixture was stirred at room temperature for 3h. After completion (monitored by TLC), the mixture was diluted using 6M HCl and neutralized by saturated sodium bicarbonate solution. Next, the solution was partitioned between water and ethyl acetate (3×). The organic layer was dried over magnesium sulfate anhydrous, filtered and concentrated in vacuo. The solid was purified by column chromatography to give the key intermediate 12f in 68% yield (Scheme S1).
	With borax buffer In ethanol; water electrolytical reduction; HMDE/SCE;
	With sodium amalgam; ethanol
	Stage #1: (4-aminophenyl)(phenyl)methanone With sodium tetrahydroborate In ethanol at 0 - 20℃; Stage #2: With ammonium chloride In ethanol; water	60 Preparation of (4-aminophenyl)(phenyl)methanol To a solution of 4-aminobenzophenone (1.00 g, 5.05 mmol) in ethanol (30 mL) in an ice bath, sodium borohydride (764 mg, 20.2 mmol) was added, and then the mixture was warmed to room temperature and stirred overnight. Saturated aqueous ammonium chloride was added thereto to quench the reaction, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride twice and brine twice dried over anhydrous magnesium sulfate, filtrated, and then the solvent was removed from the filtrate in vacuo. The residue was purified by silica gel chromatography to give 959 mg of the title compound as a light yellow oil. 1H-NMR δ (DMSO-d6); 2.24 (1H, br.), 3.64 (2H, br.), 5.74 (1H, s), 5.74 (1H, m), 6.69-6.77 (2H, m), 7.11-7.22 (1H, m), 7.23-7.40 (5H, m).
	With sodium tetrahydroborate
	With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 3h;	7 LiAlH4 (5 mmol, 189.8 mg) was added to the reaction flask and stirred at 0 °C for 15 min. After AlCl3 (5 mmol, 666.7 mg) in ether (8 ml) was added dropwise to the reaction, and the mixture was stirred at 0 °C for 5 min. A solution of p-aminobenzophenone (5a, 1 mmol, 197.2 mg) in ether (8 ml) was added dropwise to the reaction. The reaction was then carried out at room temperature for 3 h. After completion of the reaction by TLC, the reaction solution was washed with 6 M HCl diluted, and then saturated with NaHCO3. The aqueous layer was extracted with ethyl acetate (10 ml X) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated to give the compound intermediate 7a as column chromatography.
	With C₃₁H₄₅Cl₂N₃O₉Rh; isopropyl alcohol; potassium hydroxide In water for 24h; Reflux;

Reference： [1]Gomaa, Mohamed Sayed; Armstrong, Jane L.; Bobillon, Beatrice; Veal, Gareth J.; Brancale, Andrea; Redfern, Christopher P.F.; Simons, Claire [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8301 - 8313]
[2]Lanzi, Matteo; Merad, Jérémy; Boyarskaya, Dina V.; Maestri, Giovanni; Allain, Clémence; Masson, Géraldine [Organic Letters, 2018, vol. 20, # 17, p. 5247 - 5250]
[3]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - WO2017/62800, 2017, A1 Location in patent: Page/Page column 54
[4]Yang, Lingling; Ma, Xiaobo; Yuan, Chen; He, Yanying; Li, Ling; Fang, Sha; Xia, Wei; He, Tao; Qian, Shan; Xu, Zhihong; Li, Guobo; Wang, Zhouyu [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 230 - 241]
[5]Sivakumar, A.; Jayarama Reddy, S.; Krishnan, V. R. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1983, vol. 22, # 9, p. 800 - 802]
[6]Kippenberg [Chemische Berichte, 1897, vol. 30, p. 1130]
[7]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); Sumitomo Pharma (in: Sumitomo Chemical); SUMITOMO CHEMICAL COMPANY LIMITED - EP1679069, 2006, A1 Location in patent: Page/Page column 73
[8]Location in patent: experimental part Mannam, Sreedevi; Sekar, Govindasamy [Tetrahedron Asymmetry, 2009, vol. 20, # 4, p. 497 - 502]
[9]Current Patent Assignee: XIHUA UNIVERSITY - CN106496132, 2017, A Location in patent: Paragraph 0115; 0116
[10]Byrne, Joseph P.; Musembi, Pauline; Albrecht, Martin [Dalton Transactions, 2019, vol. 48, # 31, p. 11838 - 11847]

7
[ 1137-41-3 ]
[ 860594-62-3 ]

Yield	Reaction Conditions	Operation in experiment
49%	With Iodine monochloride; acetic acid at 30℃;
23%	With Iodine monochloride; calcium carbonate In methanol at 20℃; for 16h;	To a stirred solution of (4-aminophenyl)-phenyl-methanone (3 g, 15 mmol) and calcium carbonate (2.4 g, 15 mmol) in methanol (50 mL) and water (10 mL) was added ICl (3.4 g, 15 mmol). The reaction mixture was stirred at r.t. for 16 h, then concentrated in vacuo. The brown residue was partitioned between EtOAc (100 mL) and saturated sodium bisulphite solution (100 mL). The organic layer was dried (sodium sulphate), filtered and concentrated in vacuo. The residue was washed with DCM (50 mL), yielding the title compound (1.1 g, 23%) as a pale grey solid. δH (d6-DMSO) 7.99 (d, J 2.1 Hz, IH), 7.67-7.58 (m, 4H), 7.57-7.44 (m, 3H), 6.80 (d, J8.7 Hz, IH), 6.24-6.16 (m, 2H). LCMS (ES+) 324 (M+H)+.
	With dichloroamine T; acetic acid; potassium iodide

With iron(III) chloride; N-iodo-succinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In toluene at 70℃; for 20h; Inert atmosphere; regioselective reaction;

Reference： [1]Location in patent: experimental part Richter, Stephanie; Gioffreda, Barbara [Archiv der Pharmazie, 2011, vol. 344, # 12, p. 810 - 820]
[2]Current Patent Assignee: UCB - WO2010/146351, 2010, A1 Location in patent: Page/Page column 51-52
[3]Waters [Journal of the Chemical Society, 1929, p. 2108]
[4]Henry, Martyn C.; McGrory, Rochelle; Faggyas, Réka J.; Mostafa, Mohamed A. B.; Sutherland, Andrew [Organic and Biomolecular Chemistry, 2019, vol. 17, # 18, p. 4629 - 4639]

8
[ 134-85-0 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C₅₀H₇₀NO₄PPdS; C₅₀H₇₀NO₄PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere;
80%	Stage #1: 4-chlorobenzophenone With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride In tetrahydrofuran at 90℃; for 12h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
80%	With ammonium sulfate; C₃₉H₄₅FeNNiP₂; sodium t-butanolate In 2-methyltetrahydrofuran at 100℃; for 7h; Inert atmosphere; Glovebox; Autoclave;

70%	With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;
70%	Stage #1: 4-chlorobenzophenone With [(k2-P,N-di(1-adamantyl)-2-morpholinophenylphosphine)Pd(Ph)Cl]; sodium t-butanolate In 1,4-dioxane Inert atmosphere; Glovebox; Stage #2: With ammonia In 1,4-dioxane at 24℃; Inert atmosphere; Glovebox;
	With copper(I) oxide; ammonium hydroxide at 220℃;

Reference： [1]Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737]
[2]Lee, Dae-Yon; Hartwig, John F. [Organic Letters, 2005, vol. 7, # 6, p. 1169 - 1172]
[3]Green, Rebecca A.; Hartwig, John F. [Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3768 - 3772][Angew. Chem., 2015, vol. 127, # 12, p. 3839 - 3843,5]
[4]Lundgren, Rylan J.; Peters, Brendan D.; Alsabeh, Pamela G.; Stradiotto, Mark [Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4071 - 4074]
[5]Alsabeh, Pamela G.; Lundgren, Rylan J.; McDonald, Robert; Johansson Seechurn, Carin C. C.; Colacot, Thomas J.; Stradiotto, Mark [Chemistry - A European Journal, 2013, vol. 19, # 6, p. 2131 - 2141]
[6]Current Patent Assignee: DOW INC - US1946058, 1932, A

9
[ 4455-13-4 ]
[ 1137-41-3 ]
C₁₈H₂₀NO₃S⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1379 - 1388

10
[ 333-20-0 ]
[ 1137-41-3 ]
[ 16586-50-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bromine In acetic acid for 2h;
74%	With bromine; acetic acid at 0 - 25℃;	Intermediate AK: (2-Aminobenzo[d]thiazol-6-yl)(phenyl)methanone 4-Aminobenzophenone (1 .0 g,5.1 mmol) and potassium thiocyanate (1 .72 g,17.8 mmol) were dissolved in glacial acetic acid (10 mL). The solution was cooled to 0 °C. Bromine liquid (0.26 ml_,5.6 mmol) was dissolved in glacial acetic acid (4 mL) and added dropwise to the solution,maintaining a reaction temperature below 25 °C. After addition was completed,the reaction mixture was stirred overnight at r.t. The reaction mixture was neutralised with ammonium hydroxide (~20 mL) under cooling. The product was collected on the filter,washed with water (~10 mL) and cold EtOAc (~20 mL),and dried in vacuo to give the title compound as a yellow solid (956 mg,74%).1H NMR 6H (500 MHz,DMSO-d6) 8.13 (s,1 H),7.71 (m,2H),7.64 (d,J = 8.4 Hz,2H),7.56 (t,J = 7.5 Hz,2H),7.42 (d,J = 8.4 Hz,1 H),6.61 (br s,2H); LCMS (Method C): 2.76 min,(255.0,MH+).
56%	With bromine In acetic acid for 24h;

With bromine; acetic acid at 25℃; Cooling with ice;

Reference： [1]Naim, S Shawkat; Singh, Sudhir K; Sharma, Satyavan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 5, p. 494 - 498]
[2]Current Patent Assignee: REDAG CROP PROTECTION LTD; GLOBACHEM NV - WO2019/141980, 2019, A1 Location in patent: Page/Page column 62
[3]Hays; Rice; Ortwine; Johnson; Schwarz; Boyd; Copeland; Vartanian; Boxer [Journal of Pharmaceutical Sciences, 1994, vol. 83, # 10, p. 1425 - 1432]
[4]Vechorkin, Oleg; Hirt, Nathalie; Hu, Xile [Organic Letters, 2010, vol. 12, # 15, p. 3567 - 3569]

11
[ 1147550-11-5 ]
[ 1137-41-3 ]
[ 16586-50-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bromine In acetic acid for 12h; Ambient temperature;
81%	With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 18h; Irradiation;	General procedure for the synthesis of 2-aminobenzothiazoles 2 General procedure: A mixture ofaniline 1 (1 mmol), NH4SCN 2 (1.0 mmol), ruthinium (2 mol%), and CH3CN (3mL) was taken in a flask open to air and stirred at rt for 10-18 h (Table 2). Aftercompletion of the reaction (monitored by TLC), water (5 mL) was added andthe mixture was extracted with ethyl acetate (3 5 mL). The combinedorganic phase was dried over anhydrous Na2SO4, filtered, and evaporatedunder reduced pressure. The resulting crude product was purified by silica gelchromatography using a mixture of hexane/ethyl acetate (4:1) as eluent toafford an analytically pure sample of product 2. All the compounds 2 areknown and were characterized by comparison of their spectral data with thosereported in the literature.

Reference： [1]Bordi; Mor; Morini; Plazzi; Silva; Vitali; Caretta [Il Farmaco, 1994, vol. 49, # 3, p. 153 - 166]
[2]Dhar S. Yadav, Lal; Krishna Pal Singh, Rana; Singh, Manjula [Tetrahedron Letters, 2020]

12
[ 1137-41-3 ]
[ 79-30-1 ]
N-(4-benzoylphenyl)isobutyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide In tert-butyl methyl ether; ethyl acetate at 0 - 20℃; for 0.5h; Inert atmosphere;	2.2 4.2.2. Synthesis of N-(4-benzoylphenyl)isobutyramide (4b) To a cooled at 0 C solution of 4-aminobenzophenone (4c, 5.0 g,25.0 mmol) in t-butyl methyl ether (123 mL) and 40% NaOH (3 mL),isobutyryl chloride was added (3.2 mL, 30 mmol) and the newsolution was stirred for 30 min at r.t. After the completion of thereaction, the solvent was evaporated in vacuum, EtOAc was addedand the organic layer was washed with water and brine, dried withNa2SO4, filtered and evaporated in vacuum till dryness to providecompound 4b as white amorphous solid (85% yield). Rf 0.25 (Hex/EtOAc 7:3); 1H NMR (CDCl3): d 7.82 (2H, d, J 8.8 Hz), 7.81 (1H, br.s), 7.78 (2H, d, J 7.6 Hz), 7.71 (2H, d, J 8.8 Hz), 7.60 (1H, d, J 7.6 Hz),7.49 (2H, d, J 7.6 Hz), 2.64e2.54 (1H, m), 1.28 (6H, d, J 7.2 Hz); 13CNMR (CDCl3): d 195.8,175.8, 142.3, 137.9, 132.8, 132.2, 131.6, 129.8,128.3, 118.8, 36.78, 19.55; MS: 268.34 (M H).
	With triethylamine In benzene for 3h; Heating;

Reference： [1]Christodoulou, Michael S.; Zarate, Mikel; Ricci, Francesca; Damia, Giovanna; Pieraccini, Stefano; Dapiaggi, Federico; Sironi, Maurizio; Lo Presti, Leonardo; García-Argáez, Aída Nelly; Dalla Via, Lisa; Passarella, Daniele [European Journal of Medicinal Chemistry, 2016, vol. 118, p. 79 - 89]
[2]Massolini, G.; Carmellino, M. L.; Baruffini, A. [Farmaco, Edizione Scientifica, 1988, vol. 43, # 6, p. 507 - 516]

13
[ 1137-41-3 ]
[ 79-04-9 ]
[ 70110-37-1 ]

Yield	Reaction Conditions	Operation in experiment
96%
90%	In ethyl acetate for 3h; Heating;
90%	With triethylamine In 1,4-dioxane at 20℃; for 0.5h;	General experimental procedure for the synthesis of compounds 3a-c General procedure: Triethylamine (0.03 ml, 0.23 mmol) was added into a solution of commercially available starting material 2a-c (0.15 mmol) in dry dioxane (2 ml). Then, chloroacetylchloride (0.02 ml, 0.23 mmol) was injected slowly into the mixture and the mixture was stirred at RT for 30 min. About 10 ml of water was added to quench the reaction. The precipitate formed was filtered to afford 3a (0.035 g), 3b (0.036 g), or 3c (0.037 g) as a white solid, which was further purified by flash chromatography using ethyl acetate/hexane as the eluent. N-(4-Benzoylphenyl)-2-chloroacetamide (3a) Yield: 90%.1H NMR (Chloroform-d) δ 8.56 (s, 1H), 7.90-7.82 (m, 2H), 7.79 (dt, J = 8.4, 1.4 Hz, 2H), 7.76-7.68 (m, 2H), 7.61 (td, J = 7.4, 1.4 Hz, 1H), 7.50 (td, J = 7.5, 7.1, 1.4 Hz, 2H), 4.23 (d, J = 1.2 Hz, 2H). 13C NMR (Chloroform-d) δ 195.6, 164.2, 140.5, 137.6, 133.9, 132.4, 131.5, 129.91, 128.3, 119.2, 42.9. HRMS (ESI) m/z: Calculated for C15H13O2NCl [M + H]+ 274.0630; Found 274.0629.

86%	With sodium hydroxide In benzene for 1h;
63%	With triethylamine In dichloromethane for 24.5h;
47%	With triethylamine In acetone at 20℃; Cooling with ice;	3.1.2. Preparation of the Mono-chloromethyl-acetamido-Derivatives (7-12) General procedure: Mono-chloromethyl-acetamido- derivatives were preparedas described earlier [24]. Briefly: To a magneticallystirred, ice-bathed, solution or suspension of the particularcommercially available sulfanilamide or aniline (1.0 equivalent)and triethylamine (2.0 equivalents) in dry acetone (25ml), chloroacetylchloride (1.5 equivalents) in dry acetone (25ml) was gradually added over 30 minutes. The reaction mixturewas stirred at room temperature until TLC revealedcomplete consumption of the starting amine. Subsequently,the reaction mixture was poured slowly onto ice water (100ml). The precipitated crude products were purified by recrystallizationfrom acetone/water. Scheme 1 shows the preparedcompounds and their corresponding starting materials.
	In ethyl acetate for 2h; Heating;
	With triethylamine In benzene for 3h; Heating;
	With triethylamine In dichloromethane at 20℃; for 16h;

Reference： [1]Mano; Seo; Imai [Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 9, p. 2720 - 2733]
[2]Yalpani, Mansur; Hall, Laurence D. [Canadian Journal of Chemistry, 1981, vol. 59, p. 2934 - 2939]
[3]Agbowuro, Ayodeji A.; Anifowose, Abiodun; Lu, Wen; Tan, Chalet; Tripathi, Ravi; Wang, Binghe; Yang, Xiaoxiao [Medicinal Chemistry Research, 2020, vol. 29, # 7, p. 1199 - 1210]
[4]Stankovsky, Stefan; Jedlovska, Eva; Spirkova, Katarina [Collection of Czechoslovak Chemical Communications, 1993, vol. 58, # 9, p. 2211 - 2214]
[5]Oukhatar, Fatima; Eliseeva, Svetlana V.; Bonnet, Célia S.; Placidi, Matteo; Logothetis, Nikos K.; Petoud, Stéphane; Angelovski, Goran; Tóth, Éva [Inorganic Chemistry, 2019, vol. 58, # 20, p. 13619 - 13630]
[6]Abutayeh, Reem Fawaz; Almaliti, Jehad; Taha, Mutasem O. [Medicinal Chemistry, 2020, vol. 16, # 3, p. 403 - 412]
[7]Hall, Laurance D.; Yalpani, Mansur [Carbohydrate Research, 1980, vol. 78, p. C4 - C6]
[8]Massolini, G.; Carmellino, M. L.; Baruffini, A. [Farmaco, Edizione Scientifica, 1988, vol. 43, # 6, p. 507 - 516]
[9]Torrens, Antoni; Mas, Josep; Port, Adriana; Castrillo, José Aurelio; Sanfeliu, Olga; Guitart, Xavier; Dordal, Alberto; Romero, Gonzalo; Fisas, Ma. Angeles; Sánchez, Elisabeth; Hernández, Enrique; Pérez, Pilar; Pérez, Raquel; Buschmann, Helmut [Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2080 - 2092]

14
[ 1137-41-3 ]
[ 814-68-6 ]
[ 22421-62-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
37%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	General Procedure A. General procedure: The amine (1 eq.) was dissolved in DCM (5 mL/mmol) and cooled to 0°C. To the solution was added acryloyl chloride (1.2 eq.) followed by triethylamine (1.2 eq.). The solution was warmed to room temperature and stirred overnight. The solution was then washed with brine and the crude product was purified by silica gel chromatography (and recrystallization if necessary) to afford the corresponding acrylamide.
37%	In dichloromethane at 0 - 20℃;	N-(4-benzoylphenyl)acrylamide (DKM 2-117). General procedure: Following General Procedure A starting from 4-aminobenzophenone (587 mg, 3.0 mmol), product was obtained after silica gel chromatography (10% to 30% ethyl acetate in hexanes) in 37% yield as a yellow solid (275 mg). 1H NMR (400MHz, CDCl3): δ 8.77 (s, 1H), 7.80-7.73 (m, 6H), 7.57 (tt, J = 1.5, 7.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 6.46 (dd, J = 1.616.9 Hz, 1H), 6.37 (dd, J = 9.9, 16.9 Hz, 1H), 5.75 (dd, J = 1.6, 9.9 Hz, 1H). 13C NMR (100MHz, CDCl3): δ 196.3, 164.4, 142.3, 137.8, 133.0, 132.5, 131.7, 131.0, 130.0, 128.8, 128.4, 119.3. HRMS (+ESI): Calculated: 252.1019 (C16H14NO2). Observed: 252.1014.General Procedure A. The amine (1 eq.) was dissolved in DCM (5 mL/mmol) and cooled to 0oC. To the solution was added acryloyl chloride (1.2 eq.) followed by triethylamine (1.2 eq.). The solution was warmed to room temperature and stirred overnight. The solution was then washed with brine and the crude product was purified by silica gel chromatography (and recrystallization if necessary) to afford the corresponding acrylamide.

	With triethylamine In benzene for 3h; Heating;
	With triethylamine In dichloromethane at 20℃;

Reference： [1]Bateman; Nguyen; Roberts; Miyamoto; Ku; Huffman; Petri; Heslin; Contreras; Skibola; Olzmann; Nomura [Chemical Communications, 2017, vol. 53, # 53, p. 7234 - 7237]
[2]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2018/144869, 2018, A1 Location in patent: Paragraph 0633; 0634; 0636
[3]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2018/144870, 2018, A1 Location in patent: Paragraph 0645; 0647
[4]Massolini, G.; Carmellino, M. L.; Baruffini, A. [Farmaco, Edizione Scientifica, 1988, vol. 43, # 6, p. 507 - 516]
[5]Jia, Jinli; Sarker, Majher; Steinmetz, Mark G.; Shukla, Ruchi; Rathore, Rajendra [Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 8867 - 8879]

15
[ 1137-41-3 ]
[ 36210-71-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: (4-aminophenyl)(phenyl)methanone With 1-methyl-2-oxopyrrolidinium hydrogen sulfate In lithium hydroxide monohydrate at 20℃; for 0.0166667h; Grinding; Stage #2: With NaNO₂ In lithium hydroxide monohydrate at 20℃; Grinding; Stage #3: With Caswell No_. 744A In lithium hydroxide monohydrate at 20℃; Grinding;
85%	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride; NaNO₂ at 0 - 5℃; for 1h; Stage #2: With Caswell No_. 744A for 0.5h;
85%	With hydrogenchloride; Caswell No_. 744A; anhydrous Sodium acetate; NaNO₂ In lithium hydroxide monohydrate at 0℃;

	With Caswell No_. 744A; sulfuric acid; NaNO₂ 1) acetic acid, water, 0-5 deg C, 2 h; 2) acetic acid, water, 0-5 deg C, 1 h; Yield given. Multistep reaction;
	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride; NaNO₂ for 0.5h; cooling; Stage #2: With Caswell No_. 744A In lithium hydroxide monohydrate for 1h; cooling; Further stages.;
	With hydrogenchloride; Caswell No_. 744A; NaNO₂ In lithium hydroxide monohydrate at 5℃; for 1h;
	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride; NaNO₂ In dichloromethane; lithium hydroxide monohydrate at 0℃; for 0.5h; Stage #2: With Caswell No_. 744A In dichloromethane; lithium hydroxide monohydrate for 0.5h;	4.1.3. General procedure for synthesis of aromatic azides General procedure: The aromatic azides are prepared (Scheme 2) by addition of 6 NHCl solution to stirring dichloromethane solution of the appropriate amine at 0 °C followed by drop wise saturated aqueous solution of NaNO2 and the contents stirred for 30 min. To the reaction mixture, added NaN3 stirred the contents for further 30 min.The contents were allowed to attain room temperature, the two phases were separated, and the aqueous phase extracted with DCM. The combined organic layers were washed with aqueous solution of NaHCO3, followed by then brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the aryl azides which were used in the next step without further purification.
	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride; NaNO₂ In lithium hydroxide monohydrate at 0℃; for 0.666667h; Stage #2: With Caswell No_. 744A; anhydrous Sodium acetate In lithium hydroxide monohydrate at 0 - 20℃; for 1h;	4.1.5.1 Preparation of azides from amines General procedure: To a solution of particular aromatic amine, 1:1 HCl-water was added in small instalments while stirring at 0°C. After 10min, 4 equivalents of 3M sodium nitrite in water was added drop wise and after 30min 3 equivalents of 3M sodium azide and sodium acetate in water was added drop wise carefully keeping the reaction mixture at 0°C or below (Scheme 2). After completion of addition, reaction was brought to room temperature and allowed to react for one more hour and finally extracted with diethyl ether for at least three times. Organic layers were washed with saturated sodium bicarbonate solution two times, dried over anhydrous sodium sulphate and concentrated to a minimum volume under reduced pressure on rotary evaporator.

Reference： [1]Location in patent: experimental part Hajipour, Abdol Reza; Mohammadsaleh, Fatemeh [Organic Preparations and Procedures International, 2011, vol. 43, # 5, p. 451 - 455]
[2]Kamel, Eman M.; Ahmad, Ragaa A.; Moustafa, Osama S. [Journal of the Chinese Chemical Society, 2005, vol. 52, # 1, p. 149 - 153]
[3]Malik, Asif A.; Ara, Tabassum [Synthetic Communications, 2022, vol. 52, # 6, p. 888 - 897]
[4]Ohba; Kubo; Nakai; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2317 - 2320]
[5]Kitamura, Yoshiaki; Tanaka, Asami; Sato, Mutsumi; Oono, Keiji; Ikawa, Takashi; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao [Synthetic Communications, 2007, vol. 37, # 24, p. 4381 - 4388]
[6]Location in patent: experimental part Kitamura, Yoshiaki; Taniguchi, Kazumi; Maegawa, Tomohiro; Monguchi, Yasunari; Kitade, Yukio; Sajiki, Hironao [Heterocycles, 2009, vol. 77, # 1, p. 521 - 532]
[7]Majeed, Rabiya; Sangwan, Payare L.; Chinthakindi, Praveen K.; Khan, Imran; Dangroo, Nisar A.; Thota, Niranjan; Hamid, Abid; Sharma, Parduman R.; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2013, vol. 63, p. 782 - 792]
[8]Dangroo, Nisar A.; Singh, Jasvinder; Dar, Alamgir A.; Gupta, Nidhi; Chinthakindi, Praveen K.; Kaul, Anpurna; Khuroo, Mohmmed A.; Sangwan, Payare L. [European Journal of Medicinal Chemistry, 2016, vol. 120, p. 160 - 169]

16
[ 1137-41-3 ]
[ 6136-66-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2306 - 2309
[2]Synthesis,2009,p. 941 - 944
[3]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1988,vol. 42,p. 448 - 454
[4]Journal of Physical Chemistry,1995,vol. 99,p. 7388 - 7394
[5]Canadian Journal of Chemistry,2005,vol. 83,p. 213 - 219
[6]Journal of Organic Chemistry,2010,vol. 75,p. 6708 - 6711
[7]Organic Preparations and Procedures International,2011,vol. 43,p. 292 - 296

17
[ 1137-41-3 ]
[ 98-09-9 ]
[ 124400-29-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With pyridine at 25℃; for 12h;	General procedure for the synthesis of N-arylbenzenesulfonamides. Method B. General procedure: To a solution of amine (1 mmol) in 3 mL of pyridine at 0°C was slowly added the appropriate benzenesulfonyl chloride (1.1 mmol, 1.1 equiv). The mixture was stirred for 12 h at 25°C. The mixture was quenched with 2N HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated in vacuum. The crude product was purified by recrystallization and/or chromatography as noted below.
	With pyridine at 0℃; Yield given;

Reference： [1]Kril, Liliia M.; Vilchez, Valery; Jiang, Jieyun; Turcios, Lilia; Chen, Changguo; Sviripa, Vitaliy M.; Zhang, Wen; Liu, Chunming; Spear, Brett; Watt, David S.; Gedaly, Roberto [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 18, p. 3897 - 3899]
[2]Takeuchi, Kumiko; Paschal, Jonathan W.; Loncharich, Richard J. [Journal of Organic Chemistry, 1995, vol. 60, # 1, p. 156 - 168]

18
[ 1137-41-3 ]
[ 1679-47-6 ]
[ 501368-47-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trimethylaluminum In hexane; dichloromethane at 20℃; for 72h;

Reference： [1]Liang, Pi-Hui; Hsin, Ling-Wei; Cheng, Chen-Yu [Bioorganic and medicinal chemistry, 2002, vol. 10, # 10, p. 3267 - 3276]

19
[ 6318-43-0 ]
[ 1137-41-3 ]
<i>N</i>-(4-benzoyl-phenyl)-3-pyridin-4-yl-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With dmap; 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide In dichloromethane for 4h; Heating;

Reference： [1]Block, Michael H.; Boyer, Scott; Brailsford, Wayne; Brittain, David R.; Carroll, Debra; Chapman, Steve; Clarke, David S.; Donald, Craig S.; Foote, Kevin M.; Godfrey, Linda; Ladner, Anthony; Marsham, Peter R.; Masters, David J.; Mee, Christine D.; O'Donovan, Michael R.; Pease, J. Elizabeth; Pickup, Adrian G.; Rayner, John W.; Roberts, Andrew; Schofield, Paul; Suleman, Abid; Turnbull, Andrew V. [Journal of Medicinal Chemistry, 2002, vol. 45, # 16, p. 3509 - 3523]

20
[ 1137-41-3 ]
[ 479408-23-6 ]
[ 479408-28-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃;

Reference： [1]Gillet, Ludovic C. J.; Schaerer, Orlando D. [Organic Letters, 2002, vol. 4, # 24, p. 4205 - 4208]

21
[ 90-90-4 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C₅₀H₇₀NO₄PPdS; C₅₀H₇₀NO₄PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium tertiary butoxide In 1,4-dioxane at 20℃; for 36h; Inert atmosphere;
93%	Stage #1: (4-bromophenyl)(phenyl)methanone With zinc bis[bis(trimethylsilyl)amide]; tri-tert-butyl phosphine; lithium chloride In tetrahydrofuran at 70℃; for 12h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
77%	With bis(tri-o-tolylphosphine)palladium⁽⁰⁾; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium tertiary butoxide In 1,4-dioxane at 80℃; for 12h; Inert atmosphere;

75%	With Caswell No_. 744A; lithium hydroxide monohydrate; triethylamine In methanol at 60℃; for 40h; Inert atmosphere; Irradiation;
71%	With copper (I) iodide; tetrabutylphosphonium malonate; ammonia In 1,4-dioxane at 25℃; for 12h; Inert atmosphere;
62%	With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium tertiary butoxide In 1,4-dioxane at 120℃; for 24h; Autoclave; Inert atmosphere;
32%	Stage #1: (4-bromophenyl)(phenyl)methanone With copper (I) iodide; L-valine; Cs₂CO₃ In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; Stage #2: With oxygen In dimethyl sulfoxide at 90℃; for 24h; Stage #3: With hydrogenchloride In dichloromethane; lithium hydroxide monohydrate; dimethyl sulfoxide at 20℃; for 0.333333h;
76 % Chromat.	Stage #1: (4-bromophenyl)(phenyl)methanone With divinylbenzene cross-linked polystyrene Rink amine resin; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium tertiary butoxide In 1,4-dioxane; <i>tert</i>-butyl alcohol at 80℃; for 20h; Stage #2: In dichloromethane for 0.75h; Further stages.;
	Multi-step reaction with 2 steps 1: 71 percent / t-BuONa, DPPF / (DPPF)PdCl₂ / tetrahydrofuran / 3 h / 80 °C 2: 68 percent / CH₃SO₂OH / 10percent Pd-C / ethanol / Heating
	Multi-step reaction with 2 steps 1: 28 percent / t-BuONa / Pd<P(o-tol)3>2Cl₂ / toluene / 3 h / 100 °C 2: 65 percent / CH₃SO₂OH / 10percent Pd-C / ethanol / Heating
80 %Chromat.	With 2-(di-tert-butylphosphino)-1-mesityl-4,5-diphenyl-1H-imidazole; ammonia; palladium diacetate; sodium tertiary butoxide In 1,4-dioxane at 120℃; for 24h; Autoclave; Inert atmosphere;
0.10 g	With copper oxide (I); ammonium hydroxide In dimethyl sulfoxide at 90℃; for 16h; Sealed tube;	4'-Aminobutyrophenone (3). General procedure: Compound 3 was prepared by a two-step procedure similar to that of Dohner 1 and Lang.2 In the first step, to a soln. of bromobenzene (37) (5.00 g, 31.80 mmol) and anhydrous aluminum chloride (6.00 g, 45.00 mmol) at room temperature was added dropwise butyric anhydride (3.30 g, 20.86 mmol). Once the evolution of hydrogen chloride ceased, the mixture was poured onto ice water (200 ml), extracted with dichloromethane (3 × 100 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo to crude afford 4'bromobutyrophenone (51) (2.99 g), which was used without further purification. In the second step, a suspension of crude 4'-bromobutyrophenone (51) (2.99 g), cuprous oxide (0.47 g, 3.29 mmol) and aqueous ammonia (2 ml, 15 M) in dimethyl sulfoxide (2 ml) was heated in a sealed-tube at 90 °C for 16 h. The reaction was allowed to cool, diluted with ethyl acetate (50 ml), washed with water (3 × 50 ml), the separated aqueous layer further extracted with ethyl acetate (3 × 50 ml) and the combined organic phases dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo. Purification by flash chromatography (hexane:ethyl acetate, 2:1) afforded 3 as a light brown solid (0.83 g, 5.09 mmol, 16% over two steps)

Reference： [1]Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737]
[2]Lee, Dae-Yon; Hartwig, John F. [Organic Letters, 2005, vol. 7, # 6, p. 1169 - 1172]
[3]Vo, Giang D.; Hartwig, John F. [Journal of the American Chemical Society, 2009, vol. 131, # 31, p. 11049 - 11061]
[4]Casadevall, Carla; Reisner, Erwin; Vijeta, Arjun [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]
[5]Yang, Chu-Ting; Fu, Yao; Huang, Yao-Bing; Yi, Jun; Guo, Qing-Xiang; Liu, Lei [Angewandte Chemie - International Edition, 2009, vol. 48, # 40, p. 7398 - 7401][Angewandte Chemie, 2009, vol. 121, # 40, p. 7534 - 7537]
[6]Location in patent: experimental part Dumrath, Andreas; Luebbe, Christa; Neumann, Helfried; Jackstell, Ralf; Beller, Matthias [Chemistry - A European Journal, 2011, vol. 17, # 35, p. 9599 - 9604]
[7]Thomas, Christopher; Wu, Marvin; Billingsley, Kelvin L. [Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 330 - 335]
[8]Weigand, Klaus; Pelka, Sylvie [Organic Letters, 2002, vol. 4, # 26, p. 4689 - 4692]
[9]Jaime-Figueroa, Saul; Liu, Yanzhou; Muchowski, Joseph M.; Putman, David G. [Tetrahedron Letters, 1998, vol. 39, # 11, p. 1313 - 1316]
[10]Jaime-Figueroa, Saul; Liu, Yanzhou; Muchowski, Joseph M.; Putman, David G. [Tetrahedron Letters, 1998, vol. 39, # 11, p. 1313 - 1316]
[11]Location in patent: experimental part Schulz, Thomas; Torborg, Christian; Enthaler, Stephan; Schaeffner, Benjamin; Dumrath, Andreas; Spannenberg, Anke; Neumann, Helfried; Boerner, Armin; Beller, Matthias [Chemistry - A European Journal, 2009, vol. 15, # 18, p. 4528 - 4533]
[12]Rennison, David; Conole, Daniel; Tingle, Malcolm D.; Yang, Junpeng; Eason, Charles T.; Brimble, Margaret A. [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6629 - 6635]

22
[ 108-86-1 ]
[ 1137-41-3 ]
[ 4058-17-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate; CyJohnPhos In toluene; <i>tert</i>-butyl alcohol at 120℃; for 0.05h; microwave irradiation;
72%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 72h;

Reference： [1]Jensen, Thomas A.; Liang, Xifu; Tanner, David; Skjaerbaek, Niels [Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 4936 - 4947]
[2]Ottosen, Erik Rytter; Sørensen, Morten Dahl; Björkling, Fredrik; Skak-Nielsen, Tine; Fjording, Marianne Scheel; Aaes, Helle; Binderup, Lise [Journal of Medicinal Chemistry, 2003, vol. 46, # 26, p. 5651 - 5662]

23
[ 626-60-8 ]
[ 1137-41-3 ]
[4-(pyridin-3-ylamino)phenyl](phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate; XPhos In toluene; <i>tert</i>-butyl alcohol at 160℃; for 0.333333h; microwave irradiation;

Reference： [1]Jensen, Thomas A.; Liang, Xifu; Tanner, David; Skjaerbaek, Niels [Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 4936 - 4947]

24
[ 626-55-1 ]
[ 1137-41-3 ]
[4-(pyridin-3-ylamino)phenyl](phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate; XPhos In toluene; <i>tert</i>-butyl alcohol at 160℃; for 0.333333h; microwave irradiation;

Reference： [1]Jensen, Thomas A.; Liang, Xifu; Tanner, David; Skjaerbaek, Niels [Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 4936 - 4947]

25
[ 348-57-2 ]
[ 1137-41-3 ]
[4-(2,4-difluorophenylamino)phenyl](phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium t-butanolate; XPhos In toluene; <i>tert</i>-butyl alcohol at 120℃; for 0.166667h; microwave irradiation;

Reference： [1]Jensen, Thomas A.; Liang, Xifu; Tanner, David; Skjaerbaek, Niels [Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 4936 - 4947]

26
[ 29540-83-8 ]
[ 1137-41-3 ]
[ 42872-23-1 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 4936 - 4947

27
[ 119-61-9 ]
[ 1137-41-3 ]
(2-(4-aminophenyl)ethene-1,1,2-triyl)tribenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at 68℃; for 14h; Inert atmosphere;	Synthesis of 1 and 2 General procedure: Under an Ar atmosphere, a three-necked flask equipped with a magnetic stirrer was charged with zinc powder (1.6 g, 24 mmol) and 40 mL THF. The mixture was cooled to -5°C, and TiCl4 (1.3 mL, 12 mmol) was slowly added by a syringe with the temperature kept under 10°C. The suspending mixture was warmed to room temperature and stirred for 0.5 h, then heated at reflux for 2.5 h. The mixture was again cooled to -5 to 0°C, charged with pyridine (0.5 mL, 6 mmol) and stirred for 10 min. The solution of two carbonyl compounds (4-aminobenzophenone: benzophenone or 4, 4’-dimethoxybenzophenone: 4-aminobenzophenone) in 1:1.2 mole ratio in 15 mL THF was added slowly. After addition, the reaction mixture was heated to reflux until the carbonyl compounds were consumed (monitored by TLC) (about 14h). The reaction was quenched with 10% K2CO3 aqueous solution and taken up with CH2Cl2. The organic layer was collected and concentrated. The crude material was purified by flash chromatography to give the desired products.
82.3%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Cooling with ice; Reflux;	1.2 Step 2. Synthesis of Compound B: 5.8 g of zinc powder was added to a 250 mL three-necked flask, and vacuum was applied continuously for 2 to 4 times.Nitrogen gas is circulated to remove oxygen and water from the system. Under nitrogen protection, 60 mL of THF is added.Under ice salt bath conditions, 5 mL of TiCl4 was slowly added dropwise with a constant pressure dropping funnel, and stirred at room temperature for 2.5 h.Then change to ice salt bath, add 1.53mL pyridine and stir for 10min.2 g of benzophenone, 1.75 g of 4-aminobenzophenone and 40 mL of dry THF solution were added slowly.Heat to reflux overnight, stop the reaction, work up, cool to room temperature, and quench with 10% K2CO3 solution.Filtration through celite, DCM extraction (100 mL×3), combined organic phase drying and steaming.A yellow solid was obtained in a yield of 82.3%.
80%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Heating;

80%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran
74%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at 24℃; Inert atmosphere; Schlenk technique; Reflux;
72%	With titanium tetrachloride; zinc In tetrahydrofuran; pyridine Reflux;	TPE-NH2: TPE-NH2 was synthesized by the typical McMurry reaction according to the literature procedures [34]. Into a two-necked round-bound scosk (100mL) were added of zinc powder (Zn, 1.49 g, 22.8 mmol) and THF (60mL). The scosk was evacuated and flushed with dry nitrogen three times. After cooling to -5 °C, TiCl4 was slowly added. The mixture was stirred for 2.5 h at room temperature. After cooling to -5 °C again, pyridine (1.53 mL, 19.0 mmol) was added and the mixture was stirred for 10 min. Then the solution of BP (1.5 g, 7.6 mmol) and BP-NH2 (1.66 g, 9.1 mmol) in THF (40 mL) was added, the mixture was refluxed overnight. Afterwards, K2CO3 solution was added to quench the reaction. After cooling to room temperature, THF was removed by a rotatory evaporator. The solution was poured into water and extracted with DCM. The collected organic layer was dried over anhydrous Na2SO4. After filtration and solvent evaporation, the crude product was purified by silica-gel column chromatography using DCM/PE (1/2, v/v) as eluent. A pale yellow solid was obtained in 72 % yield. 1H NMR (400 MHz, CDCl3): δ 7.13-6.99 (m, 17H); 6.85-6.82 (d, 2H); 6.52-6.49 (d, 2H). 13C NMR (101 MHz, CDCl3): δ 144.69, 144.57, 144.52, 144.24, 141.25, 139.87, 135.04, 132.94, 131.89, 131.82, 131.78, 128.20, 128.12, 127.98, 127.96, 126.70, 126.54, 126.53, 115.19. IR (KBr, ν, cm-1): 3476, 3378, 3009.
51.2%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
51.6%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
38%	With titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
10%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at -10℃; for 3h; Inert atmosphere; Reflux;
	With titanium tetrachloride; zinc In tetrahydrofuran Reflux;
4.16 g	With titanium tetrachloride; zinc In tetrahydrofuran at -78 - 80℃; Inert atmosphere;	1.1; 9 1) Synthesis of compound TPE-NH2 Add zinc powder (3.3g), 4-aminobenzophenone (2.5g), benzophenone (2.5g) to a fully dried 250mL two-necked round-bottomed flask and evacuate and fill the argon gas for 3 times. 100 mL of ultra-dry tetrahydrofuran was injected under an atmosphere. The mixture was placed in a liquid nitrogen acetone bath and cooled to -78°C, and titanium tetrachloride (2.9 mL) was slowly added dropwise. After the addition was completed, the reaction mixture was continuously stirred for 15 min. The liquid nitrogen acetone bath was removed, and the reaction system was gradually returned to room temperature and stirring was continued for half an hour. Finally, it was heated to 80°C and refluxed for 12 hours. After the reaction is complete, quench the reaction with 1mol/L hydrochloric acid, filter with suction, take the filtrate, extract with ethyl acetate, spin dry, use 10:1 ratio of dichloromethane: methanol as eluent, and separate by column chromatography to obtain the compound A1: 1-(4-aminophenyl)-1,2,2-triphenylethylene (4.16g).
	With titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Schlenk technique;
	With titanium tetrachloride; zinc In tetrahydrofuran
	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran

Reference： [1]Chen, Shengxin; Qiu, Rongmao; Yu, Qiuhan; zhang, Xueyan; Wei, Ming; Dai, Zhenya [Tetrahedron Letters, 2018, vol. 59, # 27, p. 2671 - 2678]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN109369543, 2019, A Location in patent: Paragraph 0021; 0023
[3]Duan, Xin-Fang; Zeng, Jing; Lue, Jia-Wei; Zhang, Zhan-Bin [Synthesis, 2007, # 5, p. 713 - 718]
[4]Lee, Yi-Ting; Chang, Yung-Ting; Chen, Chao-Tsen; Chen, Chin-Ti [Journal of Materials Chemistry C, 2016, vol. 4, # 29, p. 7020 - 7025]
[5]Chen, Weijie; Zhang, Chen; Han, Xie; Liu, Sheng Hua; Tan, Ying; Yin, Jun [Journal of Organic Chemistry, 2019, vol. 84, # 22, p. 14498 - 14507]
[6]Li, Wen-Bo; Luo, Wei-Jian; Li, Kai-Xuan; Yuan, Wang-Zhang; Zhang, Yong-Ming [Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1300 - 1305]
[7]Cai, Yunbo; Li, Lingzhi; Wang, Zongtan; Sun, Jing Zhi; Qin, Anjun; Tang, Ben Zhong [Chemical Communications, 2014, vol. 50, # 64, p. 8892 - 8895]
[8]Wang, Yi Jia; Li, Zeyu; Tong, Jiaqi; Shen, Xiao Yuan; Qin, Anjun; Sun, Jing Zhi; Tang, Ben Zhong [Journal of Materials Chemistry C, 2015, vol. 3, # 15, p. 3559 - 3568]
[9]Liang, Chunshuang [RSC Advances, 2020, vol. 10, # 48, p. 29043 - 29050]
[10]Fan, Ying; Hu, Yuchen; Luo, Tingrong; Wu, Wen; Xia, Xuefeng; Zhang, Jinqiang; Zhang, Qianyu [Chemical Communications, 2021, vol. 57, # 93, p. 12520 - 12523]
[11]Sk, Bahadur; Patra, Abhijit [CrystEngComm, 2016, vol. 18, # 23, p. 4290 - 4294]
[12]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - WO2017/8743, 2017, A1 Location in patent: Paragraph 112
[13]Current Patent Assignee: SOUTH CHINA NORMAL UNIVERSITY - CN111116418, 2020, A Location in patent: Paragraph 0044; 0048-0052; 0086-0088
[14]Ma, Xiaoxie; Chi, Weijie; Han, Xie; Wang, Chao; Liu, Shenghua; Liu, Xiaogang; Yin, Jun [Chinese Chemical Letters, 2021, vol. 32, # 5, p. 1790 - 1794]
[15]Hu, Yi-Xiong; Li, Wei-Jian; Wang, Wei; Wang, Xu-Qing; Xu, Lin; Xu, Wei-Tao; Yang, Hai-Bo; Zhang, Dan-Yang [Angewandte Chemie - International Edition, 2021, vol. 60, # 34, p. 18761 - 18768][Angew. Chem., 2021, vol. 133, # 34, p. 18909 - 18916]
[16]Lv, Hong-Min; Jiang, Zi-Ke; Wang, Jing; Wang, Tao; Zhang, Xiao-Nan; Hu, Yi-Meng; Ma, Yan-Yan [New Journal of Chemistry, 2021, vol. 45, # 41, p. 19521 - 19530]

28
[ 36210-71-6 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 10% Pd/C; diphenyl sulfide; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;
99%	With hydrogen In methanol at 25℃; for 12h; Green chemistry; chemoselective reaction;
99%	With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;

97%	With hydrogen In methanol at 20℃; for 12h; chemoselective reaction;	4.3. Typical procedure for the chemoselective hydrogenation General procedure: The mixture of the substrate (0.250 mmol), 0.5% Pd/MS3A or 0.5% Pd/MS5A (10 wt % of the substrate) and MeOH (1 mL) was stirred under H2 atmosphere (balloon) at room temperature. After a given period, the reaction mixture was filtered through a membrane filter (Millipore, Millex-LH, 0.45 mm), and the filtrate was concentrated in vacuo to produce the corresponding reduced product.
94%	With hydrogen In methanol at 20℃; for 24h;
94%	With hydrogen In methanol at 25℃; Flow reactor; chemoselective reaction;	4.2 Typical procedure for the palladium-catalyzed hydrogenation under the flow conditions (Tables 2 and 3) General procedure: A solution of the substrates possessing reducible functional groups (1mmol) within the molecule in MeOH (20mL) was flowed at 1mL/min into the catalyst-packed cartridge (10% Pd/C, 10% Pd/HP20, 0.5% Pd/MS3A, or 0.3% Pd/BN; 30mm long-cartridge, ca. 0.3mL volume) under 1, 50, or 80bar hydrogen gas at 25, 50, 75, or 100°C using H-Cube (ThalesNano Nanotechnology Inc.). Catalyst cartridges were filled with 10% Pd/C (99.4mg), 10% Pd/HP20 (101.4mg), 0.5% Pd/MS3A (99.6mg), and 0.3% Pd/BN (99.7mg). The reaction mixture was passed through the catalyst cartridge once and MeOH (the carrier solvent) was concentrated in vacuo to give an analytically pure product. The obtained product was identified by 1H NMR measurement.
90%	With iron In water at 20℃; Inert atmosphere;	General experimental procedure for reduction of azidoarenes General procedure: The azido compound (1 mmol) was added to the freshly prepared Fe(0) nanoparticles (3 mmol) in water (5 mL) in the same pot under constant stirring at room temperature under argon atmosphere. After completion of reaction (TLC) the mixture was extracted with ethyl acetate (3 X 10 mL) (all Fe-species remained around stirring bar). Evaporation of solvent and purification by short column chromatography provided the pure product which was properly characterized by spectroscopic (IR, 1H NMR and 13C NMR) data.
89%	With palladium 10% on activated carbon; hydrogen at 20℃; for 24h; Neat (no solvent);	4.2. General procedure for the solvent-free Pd/C-catalyzed hydrogenation General procedure: In a 25-mL round-bottom flask were placed the substrate (1.00 mmol) and 10% Pd/C (10 wt % of the substrate), and the mixture was stirred using a magnetic stirrer at room temperature under a hydrogen atmosphere (balloon) for 24 h Et2O (20 mL) was added, and the mixture was passed through a membrane filter (Millipore, Millex-LH, 0.45 μm) to remove the catalyst. The filtrate was concentrated in vacuo to give the pure product.
	With hydrogen In methanol at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Mori, Akinori; Mizusaki, Tomoteru; Kawase, Masami; Maegawa, Tomohiro; Monguchi, Yasunari; Takao, Shinobu; Takagi, Yukio; Sajikia, Hironao [Advanced Synthesis and Catalysis, 2008, vol. 350, # 3, p. 406 - 410]
[2]Yabe, Yuki; Sawama, Yoshinari; Yamada, Tsuyoshi; Nagata, Saori; Monguchi, Yasunari; Sajiki, Hironao [ChemCatChem, 2013, vol. 5, # 8, p. 2360 - 2366]
[3]Esaki, Hiroyoshi; Hattori, Tomohiro; Tsubone, Aya; Mibayashi, Satoko; Sakata, Takao; Sawama, Yoshinari; Monguchi, Yasunari; Yasuda, Hidehiro; Nosaka, Kazuto; Sajiki, Hironao [ChemCatChem, 2013, vol. 5, # 12, p. 3629 - 3635]
[4]Location in patent: experimental part Takahashi, Tohru; Yoshimura, Masatoshi; Suzuka, Hiroyasu; Maegawa, Tomohiro; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao [Tetrahedron, 2012, vol. 68, # 39, p. 8293 - 8299]
[5]Maegawa, Tomohiro; Takahashi, Tohru; Yoshimura, Masatoshi; Suzuka, Hiroyasu; Monguchi, Yasunari; Sajiki, Hironao [Advanced Synthesis and Catalysis, 2009, vol. 351, # 13, p. 2091 - 2095]
[6]Hattori, Tomohiro; Tsubone, Aya; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao [Tetrahedron, 2014, vol. 70, # 32, p. 4790 - 4798]
[7]Panja, Subir; kundu, Debasish; Ahammed, Sabir; Ranu, Brindaban C. [Tetrahedron Letters, 2017, vol. 58, # 35, p. 3457 - 3460]
[8]Location in patent: experimental part Monguchi, Yasunari; Fujita, Yuki; Hashimoto, Shota; Ina, Mariko; Takahashi, Tohru; Ito, Ryo; Nozaki, Kei; Maegawa, Tomohiro; Sajiki, Hironao [Tetrahedron, 2011, vol. 67, # 45, p. 8628 - 8634]
[9]Kitamura, Yoshiaki; Tanaka, Asami; Sato, Mutsumi; Oono, Keiji; Ikawa, Takashi; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao [Synthetic Communications, 2007, vol. 37, # 24, p. 4381 - 4388]

29
[ 1137-41-3 ]
[ 1016-77-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1923,vol. 42,p. 508

30
[ 108-31-6 ]
[ 1137-41-3 ]
[ 557-24-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	Example 3 4-Aminobenzophenone (10.00 g, 0.0507 mol) was added to a stirred solution of maleic anhydride (4.98 g, 0.0508 mol) in dichloromethane (200 ml). After 10 minutes of stirring at room temperature, yellow precipitate was formed. Stirring was continued for a further 3 hours, following which the solid was collected, washed with dichloromethane (3 x 30 ml) and diethyl ether (2 x 30 ml) and finally air dried to yield the maleamic acid.(Found: C, 68.74; H, 4.57; N, 4.41%. C₁₇₁₃O₄equires C, 69.15; H, 4.44; N, 4.74%). H.p.l.c (Kromazil C₁₈ 49.95% MeOH, 49.95% H₂, 0.1% CF3O2): 99.7% lambdamax06 nm; epsilon 20560. 1-n.m.r (DMSO): delta 10.62 (1H, s, NH); 7.8 - 7.5 (9H, m, phenyl); 6.45 (1H, d; CH = CH); 6.31 (1M, d, CH = CH); 3.38 (1H, S, CO2).

Reference： [1]Patent: EP758314,1999,B1

31
Ricon 131 MA₁₇ [ No CAS ]
[ 1137-41-3 ]
poly(butadiene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene at 82℃; for 7h;	8 Example 8; Synthesis of amide-linked polymer-Bound photoinitiator (8) A solution of Ricon 131 MA17 (28 g, Sartomer), 4-aminobenzophenone (7.8 g, 39 mmol), and toluene (45 mL) were combined in a 250 mL four-necked flask equipped with a reflux condenser, internal temperature probe, and mechanical stirring under N2. The stirred mixture was heated to 82° C. for 7 h, then the solvent was removed in vacuo to yield the amide-linked polymeric photoinitiator 8 in quantitative yield. The product exhibited acceptable 1H, UV-Vis, and FT-IR spectral characteristics.

Reference： [1]Current Patent Assignee: HENKEL AG & CO. KGAA - US2003/236425, 2003, A1 Location in patent: Page 10

32
[ 5975-12-2 ]
[ 1137-41-3 ]
[ 733750-47-5 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 150℃; for 0.5h;Irradiation;	A mixture of <strong>[5975-12-2]2,4-dichloro-3-nitro-pyridine</strong> (77 mg, 0.4 mmol), 4-benzoyl-aniline (1.0 eqv, 7 9mg, 0.4 mmol) and potassium carbonate (1.4 eqv, 78 mg, 0.56 mmol) in DMF (1 ml) was stirred in a sealed vessel at 150 °C for 30 mins under microwave irradiation. HPLC provided intermediate compound 2- [4-BENZOYL-ANILINO]-4-DICHLORO-3-NITRO-PYRIDINE as brown solid (58 mg, 41 percent yield). Exact mass calculated for CL8HI2CLN303 353.06, LCMS (ESI) m/z 353.6 (M+H+, 100percent).

Reference： [1]Patent: WO2004/65380,2004,A1 .Location in patent: Page 183

33
[ 1137-41-3 ]
[ 14002-51-8 ]
N-(4-benzoylphenyl)biphenyl-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In N,N-dimethyl-formamide for 24h; Reflux;	General Procedure for the Synthesis of Biphenyl-4-carboxamide derivatives 3(b-c) and 4 (b-c) General procedure: A solution of 2 (4.4 mmol) was added to a solution containing the specified aminobenzophenone (4.4 mmol) and triethylamine (1.3 ml, 8.8 mmol) in dry DMF. The reaction mixture was refluxed for 24 h, and then cooled to rt. DMF and excess triethylamine was evaporated under reduced pressure. To the residue, 20 ml of DCM was added and the solution was stirred for 10 min. at room temperature. The filtered solution was extracted with 10 ml of water. The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was recrystallized from DCM/diethylether.
63%	With triethylamine In tetrahydrofuran at 20℃;	Synthesis of N- (4-benzophenone)-benzamide derivatives; General method for Synthesis of N- (4-benzophenone)-benzamide derivatives (STX1430-1435):; Method A:; to a stirred solution of the amine (n mmol) in THF are added triethylamine (1.2n mmol) and the acyl chloride (1.2n mmol) at room temperature. After completion, ethyl acetate and water are added. The aqueous layer is extracted by ethyl acetate. The combined organic layers are washed with brine, dried (MgS04), filtered and evaporated under reduce pressure. The crude product is then purified to give the amide.; Biphenyl-4-carboxylic acid (4-benzoyl-phenYl)-amide (STX1430. CCM01029 .; Reaction of 4-aminobenzophenone (102 mg, 0.52 mmol) in THF (6 mL) with 4- biphenylcarbonyl chloride (143 mg, 0.65 mmol) in presence of triethylamine (90 µL, 0.65 mmol) according to method A gave biphenyl-4-carboxylic acid (4-benzoyl-phenyl)-amide (125 mg, 0.33 mmol, 63% yield) as a yellow powder after purification by crystallisation in DCM/EtOAc. Rf: 0.2 (DCM); M. p.: 212-213 °C; 1H NMR (270MHz, DMSO-d6) on 7.40-7. 45 (m, 1H, HAr), 7.49 (bs, 1H, HAr), 7.52 (bs, 1H, HAr), 7.54-7. 59 (m, 2H, HAr), 7.64-7. 68 (m, 1H, HAr), 7.72 (d, 1H, J = 1.54 Hz, HAr), 7.74-7. 76 (m, 2H, HAr), 7.77-7. 79 (m, 2H, HAr), 7.81 (s, 1H, HAr), 7.87 (d, 2H, J = 8.4 Hz, HAr), 8.02 (d, 2H, J = 8.4 Hz, HAr), 8.09 (d, 2H, J = 8. 4 Hz, HAr), 10.70 (s, 1H, NH); LC/MS (AP-) m/z 376.0 (M-H); tR = 2.7 min (99.9%)

Reference： [1]Sweidan, Kamal; Engelmann, Jörn; Rayyan, Walid Abu; Sabbah, Dima; Zarga, Musa Abu; Al-Qirim, Tariq; Al-Hiari, Yusuf; Sheikha, Ghassan Abu; Shattat, Ghassan [Letters in drug design and discovery, 2015, vol. 12, # 5, p. 417 - 429]
[2]Current Patent Assignee: IPSEN SA - WO2005/42513, 2005, A1 Location in patent: Page/Page column 134-135

34
[ 34841-35-5 ]
[ 1137-41-3 ]
[ 7550-45-0 ]
[ 341526-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; aqueous potassium carbonate; ethyl acetate;	b) McMurry Reaction 4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenylamine Zinc (10.0 g, 0.154 mol) and tetrahydrofuran (THF) (120 ml) is added to the reaction vessel and cooled to -10 C. To the mixture is added dropwise titan tetrachloride (14.4 g, 0.076 mol) at about -10 C. After the addition is completed the mixture is refluxed for two hours. Then it is cooled to 40 C. and (4-Aminophenyl)phenyl-methanone (5.1 g, 0.0258 mol) and 3-chloropropiophenone (4.36 g, 0.0258 mol) are dissolved in THF (50 ml) and added to the mixture. Refluxing is continued for additional 3.5 hours. The cooled reaction mixture is poured in aqueous potassium carbonate solution (14 g K2CO3+140 ml water) and allowed to stand over night. The mixture is filtered and the precipitate is washed three times with THF. The filtrate is evaporated to dryness. The residue is dissolved in ethyl acetate and washed with water. Yield 9.6 g Z-isomer being the only isomer. Z-isomer: 1H NMR (CDCl3): 2.90 (t, 2H), 3.41 (t, 2H), 6.32 (d, 2H), 6.64 (d, 2H), 7.0-7.4 (m, 10H).

Reference： [1]Patent: US6576645,2003,B1

35
[ 374-35-6 ]
[ 1137-41-3 ]
[ 147696-09-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In N,N-dimethyl acetamide	22 N-[(4-Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide EXAMPLE 22 N-[(4-Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (10.54 g, 66 mmol) in N,N-dimethylacetamide (100 mL) was added thionyl chloride (7.94 g, 66 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 4-Aminobenzophenone (8.67 g, 44 mmol) was added in one portion and the reaction mixture stirred at room temperature overnight. The mixture was poured into water and the white solid that precipitated upon stirring was filtered from solution, dried on the filter for 1 hour, and recrystallized from ethyl acetate/hexane (1:2 v/v). The first crop yielded the title propanamide (9.51 g, 64%) as a white solid; mp 151°-153° C. A second crop was filtered upon cooling of the filtrate for 72 hours to yield an additional 3.21 g (22%) of a white solid which was identical to the first crop by melting point and spectral properties. 1 H--NMR (300 MHz, d6 --DMSO): 1.61 (s, 3H, CH3)7.54-7.59 (m, 3H, aromatic and OH), 7.65-7.71 (m, 3H, aromatic), 7.75 (d, 2H, J=8.5 Hz, aromatic), 7.98 (d, 2H, J=8.5 Hz, aromatic), 10.35 (s, 1H, NH). MS (CI, CH4): 338(M+1). Analysis for C17 H14 F3 NO3: Calculated: C, 60.54; H, 4.23; N, 4.15. Found: C, 60.33; H, 4.23; N, 4.12.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US5272163, 1993, A

36
[ 1137-41-3 ]
2-amino-5⁽⁶⁾-benzoylbenzimidazole [ No CAS ]
[ 4834-61-1 ]

Yield	Reaction Conditions	Operation in experiment
91.5%	With acetic anhydride In benzene	29.A (A) (A) 2-Amino-5(6)-benzoylbenzimidazole Three-hundred grams (1.52 mole) of 4-aminobenzophenone were added in portions to a stirred solution of 250 ml. of acetic anhydride in 250 ml. of benzene. The temperature of the mixture rose to about 70° C. The reaction mixture was stirred overnight. The preciptated product was filtered, washed with benzene and dried. The yield of 4-acetamidobenzophenone was 333.8 g. (91.5 percent yield), mp. 150°-152° C. (Lit. mp. 155° C., Chem. Abst. 55, 18651).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4118742, 1978, A

37
[ 1137-41-3 ]
1-(thiazolin-2-yl)-2-amino-5⁽⁶⁾-benzoylbenzimidazole [ No CAS ]
[ 4834-61-1 ]

Yield	Reaction Conditions	Operation in experiment
91.5%	With acetic anhydride In benzene	5 1-(Thiazolin-2-yl)-2-amino-5(6)-benzoylbenzimidazole EXAMPLE 5 1-(Thiazolin-2-yl)-2-amino-5(6)-benzoylbenzimidazole Three-hundred grams (1.52 mole) of 4-aminobenzophenone were added in portions to a stirred solution of 250 ml. of acetic anhydride in 250 ml. of benzene. The temperature of the mixture rose to about 70° C. The reaction mixture was stirred overnight. The precipitated product was filtered, washed with benzene and dried. The yield of 4-acetamidobenzophenone was 333.8 g. (91.5 percent yield), mp. 150°-152° C. (Lit. mp. 155° C., Chem Abst. 55, 18651).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4150028, 1979, A

38
[ 13472-00-9 ]
[ 67-43-6 ]
[ 1137-41-3 ]
[ 191661-01-5 ]
[ 254759-82-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of DTPA (179 mg, 0.5 mmol) in 5 mL of dry DMSO and 3 mL of dry triethylamine was added a solution of 4-aminobenzophenone (4ABP, 99 mg, 0.5 mmol) in 5 mL DMSO. The mixture was stirred for 0.5 h and treated with a solution of 4-aminophenethylamine (4APEA, 68 mg, 0.05 mmol) in 5 mL DMSO. After an additional 3 h stirring at room temperature, the mixture was evaporated to dryness. The oily residue was chromatographed on reversed-phase C18 hplc (using a step gradietn of 0-60% acetonitrile in 0.1% TFA buffer) to give 4 as a cream colored solid and 12 as a pale yellow solid. Compound 4 was obtained in 57 mg yield. 1H-NMR (CD3OD): d 3.2-3.5 (10H, m), 3.60 (2H, s), 3.63 (2H, s), 3.74 (2H, s), 4.43 (2H, s), 7.53 (2H, m), 7.62 (1H, dd), 7.76 (2H, m), 7.8 (4H, s); MS: m/z 573 (M+H). Compound 12 was obtained in 47 mg yield. 1H-NMR (CD3OD): d 2.73 (2H, t), 3.25 (2H, t), 3.3-3.5 (12H, m), 3.67 (2H, s), 3.73 (2H, s), 4.3 (2H, s), 7.23 (4H, s), 7.55 (2H, m) 7.64 (1H, dd), 7.8 (2H, m), 7.83 (4H, m); MS: m/z 691 (M+H)

Reference： [1]Patent: US6740756,2004,B1 .Location in patent: Page column 11; 12

39
[ 348-36-7 ]
[ 1137-41-3 ]
[ 1254354-83-0 ]

Reference： [1]Molecules,2010,vol. 15,p. 5840 - 5849

40
[ 6136-66-9 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetamidine hydrochloride; caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 20h;Inert atmosphere; Green chemistry;	General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with Cs2CO3 (2 or 3 mmol), MCM-41-L-proline-CuI (0.1 mmol), aryl iodide (1.0 mmol), acetamidine hydrochloride (1.2 or 2 mmol) and DMF (3.0 mL) under Ar. The reaction mixture was stirred at 130 or 140 C for 20 h. After being cooled to room temperature, the mixture was diluted with CH2Cl2 (10 mL) and filtered. The catalyst was washed with distilled water (2 × 5 mL) and EtOH (2 × 5 mL) and air dried when reused in the next run. The filtrate was concentrated with the aid of a rotary evaporator and the residue was purified by column chromatography on silica gel using petroleum ether (30-60 C)/ethylacetate (10:1 to 1:1) as eluent to give the desired product 2. All the products 2a-z are known compounds.

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 315 - 320
[2]Chemical Communications,2011,vol. 47,p. 5076 - 5078
[3]Journal of Organic Chemistry,2016,vol. 81,p. 330 - 335

41
[ 13528-93-3 ]
[ 1137-41-3 ]
[ 1336959-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-aminophenyl)(phenyl)methanone With pyridine In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1,2-bis-(chlorodimethylsilyl)ethane In dichloromethane at 20℃; for 16h;	3 Example 3: Preparation of a disilane degradable linking agentA degradable linking agent with the formula shown above can be prepared as follows:4-aminobenzophenone (2 eq) is placed in an oven-dried round-bottom flask under inert atmosphere. Anhydrous DCM and pyridine (2.5 eq) is added to the reaction mixture. The reaction mixture is allowed to stir at room temperature for 5 min. l,2-bis(chlorodimethylsilyl)methane (1 eq) is added at once via syringe and the reaction mixture is allowed to stir for additional 16 h at room temperature. Multifunctional structures are made by reacting more than 1 eq of 1 ,2- bis(chlorodimethylsilyl)methane with 4-aminobenzophenone to form a degradable linking agent having multiple photoreactive groups.

Reference： [1]Current Patent Assignee: SURMODICS INC - WO2011/123441, 2011, A1 Location in patent: Page/Page column 33-34

42
[ 1137-41-3 ]
[ 538-75-0 ]
[ 1383815-20-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With zinc(II) oxide In toluene at 80℃; for 8h;	4.3. General procedure for nano ZnO catalyzed guanylation of amines with carbodiimides listed in Table 2 and Table 3 General procedure: A mixture of amine (1 mmol), carbodiimide (1.1 mmol) and nanocrystalline ZnO (20 mol %, 0.016 g) was stirred in toluene (1 mL) at 80 °C for 8 h (for aromatic and aliphatic primary amines) or at 110 °C for 10 h (for secondary amines). The progress of the reaction was monitored by TLC analysis. At the end of the reaction, the reaction mixture was allowed to cool to room temperature, centrifuged and filtered the supernatant through a sintered funnel. The catalyst was then washed with ethyl acetate, centrifuged and filtered. The combined filtrate was concentrated under reduced pressure, and further purified by column chromatography on neutral alumina using ethyl acetate/hexane as the eluent to afford the desired product in good yields.

Reference： [1]Location in patent: experimental part Kantam, M. Lakshmi; Priyadarshini; Amal Joseph; Srinivas; Vinu; Klabunde; Nishina, Yuta [Tetrahedron, 2012, vol. 68, # 29, p. 5730 - 5737]

43
[ 1137-41-3 ]
[ 117428-49-6 ]
[ 1415919-89-9 ]

Reference： [1]Chinese Journal of Chemistry,2012,vol. 30,p. 1999 - 2008,10

44
[ 108-77-0 ]
[ 1137-41-3 ]
[ 1402603-01-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydrogencarbonate In acetone at 160℃; for 4h; Autoclave;

Reference： [1]Tehfe, Mohamad-Ali; Dumur, Frederic; Graff, Bernadette; Morlet-Savary, Fabrice; Fouassier, Jean-Pierre; Gigmes, Didier; Lalevee, Jacques [Macromolecules, 2012, vol. 45, # 21, p. 8639 - 8647]

45
[ 1061903-82-9 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide In dimethyl sulfoxide at 140℃; for 4h; Green chemistry;	General Procedure A General procedure: A reaction tube was charged with the 2-aryloxypropanamide (1.0 mmol), potassium hydroxide (112 mg, 2.0 mmol) and dimethyl sulphoxide (DMSO 4 mL). The mixture was heated at 140 C for 3-16 h. The reaction was monitored by TLC. After the reaction period, the reaction mixture was cooled, diluted with saturated brine and extracted with dichloromethane three times. The combined organic layers were washed with three portions of saturated brine and then dried over MgSO4 and filtered. Solvent was removed under reduced pressure. The product was purified through flash column chromatography on 300-400 mesh silica gel with petroleum ether/ethyl acetate as eluent
144.6 mg	With potassium hydroxide at 140℃;

Reference： [1]Yu, Jianzhong; Zhang, Peizhi; Wu, Jun; Shang, Zhicai [Tetrahedron Letters, 2013, vol. 54, # 24, p. 3167 - 3170]
[2]Yu, Jianzhong; Wang, Yongtao; Zhang, Peizhi; Wu, Jun [Synlett, 2013, vol. 24, # 11, p. 1448 - 1454]

46
[ 1137-41-3 ]
trifluoromethylsilver [ No CAS ]
[ 728-86-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride In water at 0℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: With tert.-butylnitrite at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #3: trifluoromethylsilver at -78 - 20℃; for 4h; Inert atmosphere; Schlenk technique;
87%	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride In water at 0℃; for 0.0833333h; Schlenk technique; Stage #2: With tert.-butylnitrite In water at -196 - 20℃; Schlenk technique; Inert atmosphere; Stage #3: trifluoromethylsilver In water at -78 - 20℃; for 5h; Schlenk technique; Inert atmosphere;	Trifluoromethylation Procedure 1 (Table 1); General Procedure General procedure: An oven-dried Schlenk tube (A) equipped with a magnetic stir bar was charged with AgF (132.2 mg, 1.05 mmol, 3.5 equiv), sealed with a septum, and degassed by alternating vacuum evacuation and nitrogen backfill (three times) before freshly distilled EtCN (3 mL)was added. To the resulting suspension, which was precooled to -78 °C (dry ice-acetone bath), was added TMSCF3 (149.3 mg, 1.05 mmol, 3.5 equiv) by microsyringe. The mixture was allowed towarm to r.t. and stirring was continued for an additional 15 min. In due course, AgF solid dissolved and a gray, dark solution of [Ag-CF3] formed. Another Schlenk tube (B) equipped with a magnetic stir bar was charged with the aniline (ArNH2; 0.30 mmol, 1.0 equiv) in freshly distilled EtCN (1.5 mL). To the resulting solution, which was precooled to 0 °C (ice bath), aq HCl (12 M; 50.0 μL, 0.60mmol, 2.0 equiv) was added; precipitate formed immediately. After 5 min stirring, t-BuONO (37.7 mg, 0.33 mmol, 1.1 equiv) was added by microsyringe, and the mixture was allowed to stir at 0 °C for 15 min. The resulting suspension in Schlenk tube (B) was degassed by alternating vacuum evacuation at -196 °C (liquid nitrogen), then the solution was allowed to warm to r.t. under a nitrogen atmosphere (three times), and finally cooled to -78 °C (dry ice-acetone bath). The gray, dark solution of [AgCF3] in Schlenk tube (A), which was precooled to -78 °C (dry ice-acetone bath), was added to Schlenk tube (B) (ArN2+Cl-) by syringe at -78 °C (dry ice-acetone bath) over a period of 1 h. After the addition was complete, the reaction mixture was stirred for 3 h at -78 °C (dry ice-acetone bath), allowed to warm to r.t., and stirring was continued for an additional 1 h. An off-white precipitate was observed, and the reaction mixture was diluted with EtOAc (3 mL) and filtered through a short silica gel column. The solvent was removed under reduced pressure with a rotatory evaporator, and the crude residue was purified by silica gel column chromatography to give the desired trifluoromethylation product 3. The yields of products 3a, 3f, 3g, 3l, 3o, 3r, 3x, and 3zb are based on the 19F NMR spectra with 4-F3COC6H4OMe as internal standard. Analytical data for the representative product ethyl 4-(trifluoromethyl)benzoate (3i) are provided below. Data for other products can be found in the literature.

Reference： [1]Wang, Xi; Xu, Yan; Mo, Fanyang; Ji, Guojing; Qiu, Di; Feng, Jiajie; Ye, Yuxuan; Zhang, Songnan; Zhang, Yan; Wang, Jianbo [Journal of the American Chemical Society, 2013, vol. 135, # 28, p. 10330 - 10333]
[2]Wang, Xi; Xu, Yan; Zhou, Yujing; Zhang, Yan; Wang, Jianbo [Synthesis, 2014, vol. 46, # 16, p. 2143 - 2148]

47
[ 916482-29-6 ]
[ 1137-41-3 ]
ethyl 2-((4-((4-benzoylphenyl)amino)-6-chloropyrimidin-2-yl)thio)octanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; toluene at 85℃; for 6h; Inert atmosphere;	Step c: Buchwald-Hartwig-amination The chlorinated ethyl [(pyrimidin-2-yl)sulfanyl] acetate derivatives (E1, 1 eq), the corresponding primary amine (E2, 1.2 eq), Xantphos (0.06 eq) and Na2CO3 (1.4 eq) were dissolved in toluene (10 ml) in a three neck round bottom flask, which was three times evacuated and backfilled with argon before adding the Pd2(dba)3 (0.02 equiv) and water (40 ml). The mixture was heated at 85°C for 6h. The reaction mixture was cooled to room temperature and diluted with toluene. The organic layer was separated from the water layer, dried over MgSO4 and filtered over celite. After evaporation under reduced pressure the crude product was purified by column chromatography on silica gel (n-hexane - ethyl acetate) and finally recrystallized in EtOH.
44%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 85℃; for 6h; Inert atmosphere;	Step c: Buchwald-Hartwig-amination General procedure: The chlorinated ethyl [(pyrimidin-2-yl)sulfanyl] acetate derivatives (E1, 1 eq), the corresponding primary amine (E2, 1.2 eq), Xantphos (0.06 eq) and Na2CO3 (1.4 eq) were dissolved in toluene (10 ml) in a three neck round bottom flask, which was three times evacuated and backfilled with argon before adding the Pd2(dba)3 (0.02 equiv) and water (40 ml). The mixture was heated at 85°C for 6h. The reaction mixture was cooled to room temperature and diluted with toluene. The organic layer was separated from the water layer, dried over MgSO4 and filtered over celite. After evaporation under reduced pressure the crude product was purified by column chromatography on silica gel (n-hexane - ethyl acetate) and finally recrystallized in EtOH.

Reference： [1]Lamers, Christina; Dittrich, Michaela; Steri, Ramona; Proschak, Ewgenij; Schubert-Zsilavecz, Manfred [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 4048 - 4052]
[2]Lamers, Christina; Dittrich, Michaela; Steri, Ramona; Proschak, Ewgenij; Schubert-Zsilavecz, Manfred [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 24, # 16, p. 4048 - 4052]

48
[ 540-37-4 ]
[ 199620-15-0 ]
[ 98-80-6 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With C₃₅H₂₀F₃₄NO₃^(1-)Pd⁽²⁺⁾Cl^(1-); N-ethyl-N,N-diisopropylamine In water at 140℃; for 0.25h; Microwave irradiation;	9 Carbonylative Suzuki-Miyaura coupling of aryl halideand arylboronic acid: general procedure General procedure: A mixture of the aryl halide (0.6 mmol), arylboronic acid (2.5 equiv), Mo(CO)6 (1.5 equiv), DIPEA (3.0 equiv), palladacycle 1 (1 mol % Pd), and water (1.0 mL) was heated in a pressure tube at 140 °C under microwave irradiation. The reaction was monitored by TLC. When the reaction has completed, the reaction mixturewas cooled to room temperature, poured into EtOAc (20 mL) and washed successively with water (310 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude product was then purified by column chromatography to give pure 4.

Reference： [1]Ang, Wei Jie; Lo, Lee-Chiang; Lam, Yulin [Tetrahedron, 2014, vol. 70, # 45, p. 8545 - 8558]

49
[ 873-74-5 ]
[ 98-80-6 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With trifluorormethanesulfonic acid; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine In water at 60℃; for 2h;	General procedure for addition of arylboronic acids to nitrile General procedure: To a mixture of arylboronic acid (1.2 mmol), nitrile (1.0 mmol), Pd(OAc)2 (4 mol%)and L1 (4 mol%), H2O (1.2 mL) and triflic acid (0.4 mL) were added and stirred at 60 °Cunder air for desired time (TLC monitoring). Then the reaction mixture was neutralized withsaturated NaHCO3 solution and extracted with ether. The combined ether solution waswashed with brine, dried by Na2SO4 and concentrated. The residue was purified by flashcolumn chromatography on silica gel using petroleum ether/cetone or petroleum ether/DCMas eluent to give the desired product.

Reference： [1]Das, Tuluma; Chakraborty, Amarnath; Sarkar, Amitabha [Tetrahedron Letters, 2014, vol. 55, # 52, p. 7198 - 7202]

50
[ 321-14-2 ]
[ 1137-41-3 ]
N-(4-benzoylphenyl)-5-chloro-2-hydroxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With phosphorus trichloride In chlorobenzene at 120℃; for 0.366667h; Microwave irradiation;	1 Synthesis of salicylanilides 2 General procedure: Salicylanilides 2 were prepared by the reaction of the appropriatesubstituted salicylic acids (5 mmol) and the substituted anilines(5 mmol) in the presence of phosphorus trichloride(2.5 mmol) in chlorobenzene [19]. The reaction was carried outwith vigorously stirring in a microwave reactor (MicroSYNTH MLSETHOS 1600 URM) for 22 min to reflux. The reaction mixture wasfiltered while hot, let stand at 20 C and then at 4 C for 24 h. Thecrude productwas filtered off and once or more times recrystallizedfrom aqueous ethanol to obtain the pure product. The mother liquorwas partly evaporated to the crystallization to obtain thesecond portion of crude product.
	With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene for 1h; Inert atmosphere; Reflux;	2.1. Compound synthesis General procedure: Anilide synthesis. General method. To a 100 mL flask equipped with a reflux condenser was added 5-chloro-2-hydroxybenzoic acid (1 equiv), the aniline derivative (1 equiv), and dry xylenes(stored over 3A molecular sieves, 40 mL per gram of 5-chloro-2-hydroxybenzoic acid) under an Argon atmosphere. The mixture was heated to reflux, and PCl3 (0.4 equiv) was added rapidly via syringe. The mixture was heated at reflux for 1 h and cooled to room temperature. Water (40 mL per gram of 5-chloro-2-hydroxybenzoic acid) was added and the resultant heterogeneous mixture stirred rapidly for 1 h. Saturated sodium bicarbonate was added to a final pH of 3-4, and the mixture stirred rapidly overnight. The solids were filtered and washed sequentially with water, toluene and hexane. Samples were analyzed by NMR, HPLC/mass spectrometry and TLC. Purification by crystallization or column chromatography on silica gel was performed when purity was less than 95% by LC. Additional experimental procedures and analytical data are provided in Supplemental data.

Reference： [1]Baranyai, Zsuzsa; Krátký, Martin; Vinšová, Jarmila; Szabó, Nóra; Senoner, Zsuzsanna; Horváti, Kata; Stolaříková, Jiřina; Dávid, Sándor; Bosze, Szilvia [European Journal of Medicinal Chemistry, 2015, vol. 101, p. 692 - 704]
[2]Mook, Robert A.; Wang, Jiangbo; Ren, Xiu-Rong; Chen, Minyong; Spasojevic, Ivan; Barak, Larry S.; Lyerly, H. Kim; Chen, Wei [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5829 - 5838]

51
[ 6579-54-0 ]
[ 1137-41-3 ]
N-4-benzoylphenyl 2,6-dichlorobenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With pyridine; at 25℃; for 12h;	General procedure: To a solution of amine (1 mmol) in 3 mL of pyridine at 0C was slowly added the appropriate benzenesulfonyl chloride (1.1 mmol, 1.1 equiv). The mixture was stirred for 12 h at 25C. The mixture was quenched with 2N HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated in vacuum. The crude product was purified by recrystallization and/or chromatography as noted below.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3897 - 3899

52
[ 60230-36-6 ]
[ 1137-41-3 ]
N-4-benzoylphenyl 2,6-difluorobenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine; at 25℃; for 12h;	General procedure: To a solution of amine (1 mmol) in 3 mL of pyridine at 0°C was slowly added the appropriate benzenesulfonyl chloride (1.1 mmol, 1.1 equiv). The mixture was stirred for 12 h at 25°C. The mixture was quenched with 2N HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated in vacuum. The crude product was purified by recrystallization and/or chromatography as noted below.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3897 - 3899

53
[ 33091-15-5 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
26%	With palladium 10% on activated carbon; chlorobenzene; potassium hydroxide In methanol; water at 60℃; for 2h; Inert atmosphere;	Procedure General procedure: The starting alcohol (1 mmol), KOH (3.0mmol) and catalyst (10 mol% Pd) were added to a Schlenkflask. In another Schlenk flask, the oxygen in the solvent(MeOH : H2O = 5:1, v/v, 6.0 mL) was removed by the freezepump-thaw and purging method. The aqueous solvent was transferred to the reaction flask of the starting alcohol by cannulation. Afterwards, chlorobenzene (3.0 mmol) was added using a syringe, and the reaction was kept under argon. Upon completion of the reaction based on TLC monitoring, the Pd/C was filtered off on celite and the solvent was removed by rotary evaporation. A brine solution was added to the residue and the product was extracted using methylene chloride. The organic layer was collected, dried with anhydrous magnesium sulfate, and concentrated byrotary evaporation. The mixture was purified via column chromatography using various hexane/EtOAc eluent systems. All products were known and characterized by comparing their 1H NMR spectra with those that have been published in the literature.

Reference： [1]Lim, Minkyung; Oh, Seungchan; Rhee, Hakjune [Bulletin of the Korean Chemical Society, 2011, vol. 32, p. 3179 - 3182]

54
[ 1137-41-3 ]
[ 93-55-0 ]
(Z)-4-(1,2-diphenylbut-1-en-1-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With titanium tetrachloride; zinc In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Reflux;	8 4.2.3.1. Synthesis of (Z)-N-(4-(1,2-diphenylbut-1-en-1-yl)phenyl)isobutyramide(6a) and (E)-N-(4-(1,2-diphenylbut-1-en-1-yl)phenyl)isobutyramide (7a) General procedure: To a cold at 10 C suspension of Ζn (1.2 g,18 mmol) in ΤF (18 mL), TiCl4 (0.82 mL, 7.5 mmol) was addeddropwise and the new mixture was stirred for another 10 min inthe same temperature and after was refluxed for 2 h. Then, a solutionof keto-amide 4b (0.50 g, 1.9 mmol) and propiophenone (5a,0.28 g, 2.1 mmol) in ΤF (37 mL), was added to the cooled suspensionof the titanium reagent at 0 C, and the reaction mixturewas refluxed for 2.5 h. After the completion of the reaction, thereaction mixture was cooled to r.t. and poured into a 10% aq K2CO3solution (15 mL). Vigorous stirring was maintained for 5 min, andthe dispersed insoluble material was removed by vacuum filtrationusing celite. The organic layer was separated and the aqueous layerwas extracted 3 times with EtOAc. The combined EtOAc extractswere washed with water and brine, dried with Na2SO4, filtered andevaporated. The residue was purified by flash column chromatography(Hex/EtOAc 8:2) to provide a mixture of the 2 diastereomers6a and 7a (86% total yield). The 2 diastereomers were separated bycrystallization from MeOH to provide compound 6a as crystals andcompound 9a as white amorphous solid in a ratio 6a/7a 3

Reference： [1]Christodoulou, Michael S.; Zarate, Mikel; Ricci, Francesca; Damia, Giovanna; Pieraccini, Stefano; Dapiaggi, Federico; Sironi, Maurizio; Lo Presti, Leonardo; García-Argáez, Aída Nelly; Dalla Via, Lisa; Passarella, Daniele [European Journal of Medicinal Chemistry, 2016, vol. 118, p. 79 - 89]

55
[ 5274-70-4 ]
[ 1137-41-3 ]
{4-[(2-hydroxy-3-nitrobenzylidene)amino]phenyl}(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1-n-butyl-3-methylimidazolim bromide; for 0.25h;	General procedure: To an equimolar dry mixture of substituted benzaldehydes1(a-j) and 4-amino benzophenone (4) in a semi-microboiling tube, 6.5 mmol of [bmim]Br was added and the mixturewas grounded uniformly in an oil bath for 10-20 min.After completion of the reaction as evident by TLC, the reactionmixture cooled down, extracted using diethyl ether and dried over MgSO4. Diethyl ether was evaporated in vacuo toafford the crude compounds. The Schiff bases 5(a-j) werethereafter recrystallized from boiling toluene in excellentyields (79-92%) and isolated [bmim]Br was employed forthe next reaction using similar conditions.

Reference： [1]Medicinal Chemistry,2016,vol. 12,p. 527 - 536

56
sodium (phenyltrihydroxyborate) [ No CAS ]
[ 16106-38-0 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In water; toluene at 60℃; for 24h; Inert atmosphere;	4.1.2 General procedure for the Suzuki-Miyaura acylation reactions General procedure: The corresponding borate salt (1mmol), Pd(PPh3)4 (0.01mmol, 11.56mg), degassed toluene (2.0mL), degassed water (0.50mL) were place in a 50mL round-bottomed flask with a magnetic stirrer bar and a rubber septum. The content of the flask was kept under argon while acyl chloride (1.10mmol), dissolved in degassed toluene (1.0mL), was added dropwise via a syringe and the flask was heated to 60°C on the oil bath. After 24h, the reaction mixture was filtered and solvent removed under vacue. The resulting residue was dissolved in DCM and was purified using flash-column chromatography or centrifugal preparative thin-layer chromatography (chromatotron) using Hexane: Ethyl acetate (9:1) as an eluent.

Reference： [1]Sithebe, Siphamandla; Molefe, Patience [Journal of Organometallic Chemistry, 2017, vol. 846, p. 305 - 311]

57
[ 1111-67-7 ]
[ 540-72-7 ]
[ 1137-41-3 ]
4-benzoylphenyl thiocyanate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Synthesis of arene diazonium tetrafluoroborates. In a 50 mL round-bottomed flask, the aniline (20 mmol) was dissolved in a mixture of absolute ethanol (20 mL) and an aqueous solution of HBF4 (50%, 5.0 mL, 40 mmol). Afterwards tert-butyl nitrite (4.8 mL, 40 mmol) was added dropwise to the solution at 0 C. The reaction was stirred at room temperature for 1 h, followed by the addition of diethyl ether (50 mL) to precipitate the arenediazonium tetrafluoroborate that was then filtered off and washed with diethyl ether (3 × 20 mL). After it had been dried in vacuo (10-3 mbar) for 10 minutes, it was directly used without further purification. Caesium carbonate (1.0 eq.), sodium thiocyanate (1.5 eq.), and <strong>[1111-67-7]copper(I) thiocyanate</strong>(1.0 eq.) were suspended in acetonitrile (0.67 M), and the mixture was cooled to 0 C.To this suspension was added dropwise a solution of the arenediazonium salt (1.0 -1.2 eq.) in acetonitrile (0.40 M), and the resulting mixture was first stirred for 1 h at 0 Cand then overnight at room temperature. Afterwards diethyl ether (30 mL) was addedand the precipitate was filtered off. The filtrate was washed with water (2 × 30 mL) andthe organic layer was dried with magnesium sulphate. The product was purified bycolumn chromatography (SiO2, cyclohexane/ethyl acetate gradient).

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 198,p. 89 - 93

58
[ 1137-41-3 ]
4,4'-(1,2-diphenylethene-1,2-diyl)dianiline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With titanium(IV) tetrachloride; zinc powder In tetrahydrofuran at 0℃; for 5h; Inert atmosphere; Reflux;
87%	With titanium(IV) tetrachloride; zinc powder In tetrahydrofuran for 5h; Inert atmosphere; Reflux;	1-5 The present invention also provides a process for producing the raw material compound 1, i.e., 1,2-(4-aminophenyl)-1,2-stilbene, which is required for the present invention, and the specific steps are as follows: Under nitrogen protection, 1 to 12 g of titanium tetrachloride (5.3 to 63.3 mmol) was slowly added to 0.5 to 5.9 g of 4-aminobenzophenone (2.5 to 30 mmol) and 0.3 to 4.2 g of zinc powder (5.3~65mmol) in tetrahydrofuran (80mL) solution under ice bath conditions, then the ice bath was removed and the mixed solution was heated to reflux for 5 h. The reaction solution was cooled to room temperature, and the reaction was quenched by adding a saturated potassium carbonate solution. The reaction solution was extracted with dichloromethane several times, and the organic phase was combined and dried over anhydrous sodium sulfate. The sodium sulfate was filtered, the filtrate was spin dried, and the obtained crude product was isolated on silica gel column to obtain compound 1, and five specific examples of the reaction are provided below.
51%	With titanium(IV) tetrachloride; zinc powder In tetrahydrofuran at 0 - 80℃; Inert atmosphere;

	With titanium(IV) tetrachloride; zinc powder
2.5 g	With titanium(IV) tetrachloride; zinc powder In tetrahydrofuran at -78℃; Reflux;
	With pyridine; titanium(IV) tetrachloride; zinc powder for 20h; Reflux; Inert atmosphere;	2.2.1. Synthesis of TPE(NH 2 ) 2 The synthesis route is shown in Scheme 1 . The synthesis is based on the McMurray reaction. Zn powder (3.90 g, 0.06 mol) was added to anhydrous THF (60 mL) in a three-necked round bottom flask under N 2 atmosphere. TiCl 4 (2.7 mL) was injected slowly under ice salt bath. The mixture was refluxed for 2 h. After cooling to room temperature, (4-Amino-phenyl)phenyl-methanone (2.37 g, 12.00 mmol), pyridine (2 mL) were added to the mixture. After stirring and refluxing for 20 h. the solution of 10% K 2 CO 3 was added into the mixture under stirring condition.The solution was extracted with CH 2 Cl 2 (3 ×20 mL), and the organic layer was collected. The combined organic fractions were washed with satu- rated brine. The solvent of the organic fractions was removed by rotary evaporators. The crude product was further purified by col- umn chromatography with silica gel as adsorbed phase and with ethyl acetate/petroleum ether = 1:1, the product yield is 54.96%. 1 H NMR (400 MHz, DMSO-D6) 7.25-6.71 (m, 12H), 6.63-6.44 (m, 4H), 6.35-6.17 (m, 4H), 4.96 (s, 4H), as shown in Figure S1.

Reference： [1]Peng, Hui-Qing; Zheng, Xiaoyan; Han, Ting; Kwok, Ryan T. K.; Lam, Jacky W. Y.; Huang, Xuhui; Tang, Ben Zhong [Journal of the American Chemical Society, 2017, vol. 139, # 29, p. 10150 - 10156]
[2]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN109206374, 2019, A Location in patent: Paragraph 0051-0054
[3]Tian, Tian; Hu, Rongrong; Tang, Ben Zhong [Journal of the American Chemical Society, 2018, vol. 140, # 19, p. 6156 - 6163]
[4]Ma, Jing; Wang, Yuxiang; Li, Xiaojing; Yang, Lan; Quan, Yiwu; Cheng, Yixiang [Polymer, 2018, vol. 143, p. 184 - 189]
[5]Hadjichristidis, Nikos; Jiang, Yu [Angewandte Chemie - International Edition, 2021, vol. 60, # 1, p. 331 - 337][Angew. Chem., 2021, vol. 133, # 1, p. 335 - 341,7]
[6]Feng, Haitao; Liu, Weiguo; Niu, Xiaoling; Wu, Xiaojing; Zhang, Hong; Zhu, Shengbo [Journal of Molecular Structure, 2022, vol. 1259]

59
[ 21856-94-0 ]
[ 1137-41-3 ]
phenyl(4-(p-tolylselanyl)phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tert.-butylnitrite; iron In dimethyl sulfoxide at 30℃; for 8h; Inert atmosphere;	Representative experimental procedure for the reaction of p-anisidine and diphenyl diselenide for the synthesis of (4-Methoxyphenyl)(phenyl)selane (Scheme 3, 3d): General procedure: A mixture of p-anisidine (1.0 mmol, 123 mg), t BuONO (1.1 mmol, 113.3 mg), diphenyl diselenide (0.5 mmol, 156 mg), freshly prepared Fe(0) catalyst (1 mmol) and DMSO (3 mL) was stirred under room temperature (30 °C) for 8 hours (TLC) under argon atmosphere and the product was extracted by ethyl acetate. The extract was washed with water (20 mL) and brine (20 mL). Then the organic phase was dried over Na2SO4 and evaporated to leave the crude product which was purified by column chromatography over silica gel (hexane/ethyl acetate 98:2) to provide the pure (4-methoxyphenyl)(phenyl)selane 3 as a gummy liquid (215 mg, 82%).

Reference： [1]Panja, Subir; Maity, Pintu; Kundu, Debasish; Ranu, Brindaban C. [Tetrahedron Letters, 2017, vol. 58, # 35, p. 3441 - 3445]

60
[ 108-86-1 ]
[ 201230-82-2 ]
[ 89415-43-0 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; Sealed tube;	4.1. The process of Pd-Pt NDs catalyzed ligand-free carbonylative Suzukicross-coupling General procedure: General procedure: a 50 mL ask equipped with a magnetic stir bar was charged with aryboronic acid (1 mmol, 1 equiv), aromatic halides (1.2 mmol, 1.2 equiv), catalyst (2 mol%), base (2 mmol, 2 equiv), DMF (5 mL) solution under CO (1 atm) atmosphere, along with sealed the reaction flask by a rubber stopper and CO was injected into it with a stainless steel gas flowmeter. The mixture was then stirred at 120 °C forthe indicated time (SI, Fig. S1). After being allowed to cool to roomtemperature, the reaction mixture was diluted with 5 mL water and extracted with diethyl ether (3 × 5 mL). The organic phases werecombined, and the volatile components were evaporated in a rotaryevaporator. The residue was puried by column chromatography onsilica gel.

Reference： [1]Wang, Zheng-Jun; Wang, Xue-Yan; Wang, Xia; Liang, Zhi-Wu; Xu, Xinhua [Catalysis Communications, 2017, vol. 101, p. 10 - 14]

61
[ 201230-82-2 ]
C₁₅H₁₄N₂O₂S [ No CAS ]
[ 1137-41-3 ]
C₂₉H₂₃N₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,4-diaza-bicyclo[2.2.2]octane; oxygen; palladium diacetate; sodium iodide at 50℃; for 12h;	23 Example 23 Compound 23: A 25 mL reaction flask was sequentially charged with palladium acetate (0.001 mmol), amine 1 w (0.5 mmol), amine 1w '(2.0 mmol), triethylenediamine (0.1 mmol), sodium iodide (0.25 mmol) and polyethylene glycol-200 (2.0 g) were introduced and a largeAtmospheric carbon monoxide and oxygen (1: 1) were reacted at 50 ° C for 12 h. Cool to room temperature, extract and evaporate the solvent under reduced pressureIsolated 83% yield.

Reference： [1]Current Patent Assignee: NANJING UNIVERSITY - CN107417478, 2017, A Location in patent: Paragraph 0077; 0078

62
[ 110-88-3 ]
[ 1137-41-3 ]
4-ethylaminobenzophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Inert atmosphere;	General Experimental Procedure General procedure: All reactions werecarried out according to the procedure written below unless otherwise noted. The starting anilines (0.1 mmol) in dryCH2Cl2 (2.5 mL) was treated with carboxylic acid (1.3 mmol)and NaBH(OAc)3 (1.6 mmol) at room temperature overnight.Saturated aqueous NaHCO3 was dropped into the reactionmixture, and then the mixture was stirred until the foaming stopped. After extracting with EtOAc, the organic layerwas dried over MgSO4. Removal of solvent from EtOAcextract under reduced pressure by a rotary evaporator gavecrude products that were purified by column chromatography. The obtained products, 4-chloro-N,N-diethylaniline (2),)N-ethylindoline (7),) 1-(4-ethylaminophenyl) ethanone (9),)4-ethylaminobenzophenone (14),) and N-(4-chlorophenyl)-5-methyl-2-pyrrolidone (18)) were confirmed by the previously reported spectroscopic data.

Reference： [1]Tamura, Satoru; Sato, Keigo; Kawano, Tomikazu [Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 1, p. 101 - 103]

63
[ 1111-67-7 ]
[ 333-20-0 ]
[ 1137-41-3 ]
4-benzoylphenyl thiocyanate [ No CAS ]

Reference： [1]Annals of Clinical Microbiology and Antimicrobials,2017,vol. 16

64
4-thiomorpholinyl-1,8-naphthalic anhydride [ No CAS ]
[ 1137-41-3 ]
C₂₈H₂₂N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With acetic acid In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere;	11.2 (2) Synthesis of Compound 11 59.8 mg (0.2 mmol) of the intermediate A2 was dissolved in 10 mL of DMF, 44.5 mg (0.24 mmol) of 4-aminodiphenyl ether was added, and 2 mL of AcOH was added.The reaction was refluxed at 100°C with nitrogen, the reaction was traced on a spot plate (approximately 16 h), quenched with 100 mL of water, and suction filtered to give a solid.The crude product was separated on a column of petroleum ether:ethyl acetate=2:1 to give Compound 11 in a yield of 62%.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN107540608, 2018, A Location in patent: Paragraph 0154; 0157; 0158

65
[ 90-96-0 ]
[ 1137-41-3 ]
C₂₈H₂₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at 68℃; for 14h; Inert atmosphere;	Synthesis of 1 and 2 General procedure: Under an Ar atmosphere, a three-necked flask equipped with a magnetic stirrer was charged with zinc powder (1.6 g, 24 mmol) and 40 mL THF. The mixture was cooled to -5°C, and TiCl4 (1.3 mL, 12 mmol) was slowly added by a syringe with the temperature kept under 10°C. The suspending mixture was warmed to room temperature and stirred for 0.5 h, then heated at reflux for 2.5 h. The mixture was again cooled to -5 to 0°C, charged with pyridine (0.5 mL, 6 mmol) and stirred for 10 min. The solution of two carbonyl compounds (4-aminobenzophenone: benzophenone or 4, 4’-dimethoxybenzophenone: 4-aminobenzophenone) in 1:1.2 mole ratio in 15 mL THF was added slowly. After addition, the reaction mixture was heated to reflux until the carbonyl compounds were consumed (monitored by TLC) (about 14h). The reaction was quenched with 10% K2CO3 aqueous solution and taken up with CH2Cl2. The organic layer was collected and concentrated. The crude material was purified by flash chromatography to give the desired products.
17%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at 90℃; Reflux; Inert atmosphere;

Reference： [1]Chen, Shengxin; Qiu, Rongmao; Yu, Qiuhan; zhang, Xueyan; Wei, Ming; Dai, Zhenya [Tetrahedron Letters, 2018, vol. 59, # 27, p. 2671 - 2678]
[2]Zhang, Shouxiang; Liu, Mengjie; Tan, Lewis Yi Fong; Hong, Quentin; Pow, Ze Liang; Owyong, Tze Cin; Ding, Siyang; Wong, Wallace W. H.; Hong, Yuning [Chemistry - An Asian Journal, 2019, vol. 14, # 6, p. 904 - 909]

66
[ 50668-21-8 ]
[ 1137-41-3 ]
C₄₁H₃₃N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With palladium diacetate; caesium carbonate; tri-t-butylphosphonium tetraphenylborate complex In toluene at 100℃; for 48h;	Synthesis of 2CZPh: General procedure: A mixture of aniline (30.3 mg, 0.325 mmol), 1 (202.2 mg, 0.629 mmol), cesium carbonate(930.3 mg, 2.85 mmol), palladium(II) acetate (3.3 mg, 0.015 mmol), and tri-tert-butylphosphoniumtetraphenylborate ((t-Bu3)PHBPh4 ; 17.9 mg, 0.0324 mmol) in dry toluene (10 mL) was stirred for48 h at 100 °C. After cooling to room temperature, the reaction mixture was filtered to removeinsoluble materials. The filtrate was concentrated by evaporation and the crude product was purifiedby column chromatography on silica gel (eluent: hexane : benzene = 7 : 3 by volume) and driedunder vacuum to afford 2CZPh as a pale green powder (yield = 70.3 mg, 46%), which was furtherpurified by recrystallization from dichloromethane-hexane to give crystalline powder.

Reference： [1]Tani, Keita; Yashima, Toru; Miyanaga, Kanae; Hori, Kazushige; Goto, Kenta; Tani, Fumito; Habuka, Yume; Suzuki, Katsuaki; Shizu, Katsuyuki; Kaji, Hironori [Chemistry Letters, 2018, vol. 47, # 9, p. 1236 - 1239]

67
[ 1137-41-3 ]
[ 84358-13-4 ]
tert-butyl 4-(4-benzoylphenylcarbamoyl)piperidine-1-carboxylic acid ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With pyridine; thionyl chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: (4-aminophenyl)(phenyl)methanone With triethylamine In dichloromethane at 20℃; for 6h; Inert atmosphere;	4.1.4. General procedure C for preparation of amide compounds(20a-c, 21a-q) General procedure: To a 50mL three-necked flask was added piperidine-carboxylicacid (12 mmol) and anhydrous DCM (25 mL), followed by theaddition of pyridine(30 mmol) and SOCl2 (14 mmol) under N2 atmosphere.After stirred at R.T. for 30min, the mixture was addedprimary amine and triethylamine dissolved in DCM (15 mL) dropwise.The reactionwas further stirred at RT for 6 h and diluted withbrine (30 mL). The organic layer was collected, and the aqueouslayer was extracted with DCM. The combined organic layers were dried over anhydrous Na2SO4and concentrated. The residue waspurified by silica gel chromatography.

Reference： [1]Dong, Xiao-Wu; Zhang, Jian-Kang; Xu, Lei; Che, Jin-Xin; Cheng, Gang; Hu, Xiao-Bei; Sheng, Li; Gao, An-Hui; Li, Jia; Liu, Tao; Hu, Yong-Zhou; Zhou, Yu-Bo [European Journal of Medicinal Chemistry, 2019, vol. 164, p. 602 - 614]

68
[ 1137-41-3 ]
[ 586-78-7 ]
[ 210965-65-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: (4-aminophenyl)(phenyl)methanone; para-nitrophenyl bromide With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; XPhos In isopropyl alcohol at 110℃; for 24h; Inert atmosphere; Stage #2: With potassium <i>tert</i>-butylate; bis(pinacol)diborane In isopropyl alcohol at 110℃; for 4h; Inert atmosphere; chemoselective reaction;	A 4.2. General procedure A General procedure: In a dried schlenk flask (25 mL in volume) equipped with a stirring bar were placed with 1-bromo-4-nitrobenzene (0.275 mmol, 1.1 eq.), Pd2(dba)3 (2.3mg, 0.0025 mmol, 1 mol%), XPhos (5.9 mg, 0.0125 mmol, 5 mol%), K2CO3 (69.1 mg, 0.5 mmol, 2.0 eq.) and arylamines (0.25 mmol, 1.0 eq., if solid). After evacuation and refill with dry nitrogen for three times, arylamines (0.25 mmol, 1.0 eq., if liquid) and iPrOH (1.0 mL) were added with syringes under a stream of nitrogen. The resulting mixture was allowed to stir at 110°C for 24 h. Then, B2pin2 (1.0 mmol, 4.0 eq.) and KOt-Bu (0.5 mmol, 2.0 eq.) were added and the mixture was then stirred in the preheated oil bath at 110°C for 4 h. After cooling to room temperature, the crude production was diluted with ethyl acetate and then washed with saturated NaCl solution. The organic layers dried over anhydrous Na2SO4, concentrated in vacuo, and purified by flash column chromatograph to give the pure products.

Reference： [1]Liang, Xueting; Xu, Liang; Li, Cuihua; Jia, Xin; Wei, Yu [Tetrahedron, 2019, vol. 75, # 6, p. 721 - 731]

69
[ 1137-41-3 ]
[ 6780-49-0 ]
potassium N-phenyl-N'-(4-phenylcarbonylphenyl)formamidinate [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 1970 - 1978

70
[ 1137-41-3 ]
[ 6780-49-0 ]
N-(4-phenylcarbonylphenyl)-N’-phenylformamidine [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 1970 - 1978

71
[ 1137-41-3 ]
[ 230955-75-6 ]
4-(4-benzoylphenylamino)-7-methoxyquinazolin-6-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.1%	In isopropyl alcohol; at 70℃; for 3h;	4-chloro-7-methoxyquinazoline-6-yl acetate (5.0 g, 19.7 mmol) and 4-aminobenzophenone (7.6g, 39.5mmol) was dissolved in isopropanol (100mL),Heated to 70 C and stirred for 3.0h, cooled to 25 C,A large amount of solids precipitated, filtered the solids,Drying under reduced pressure gave 7.0 g of a white solid with a yield of 86.1%.

Reference： [1]Patent: CN104761507,2019,B .Location in patent: Paragraph 0566; 0569-0571

72
[ 1137-41-3 ]
C₁₃H₇⁽²⁾H₄NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With C₄₀H₅₁ClIrN₃; potassium carbonate; deuterium In dichloromethane at 50℃; for 12h; Sealed tube; Inert atmosphere; regioselective reaction;

Reference： [1]Cao, Lei; Huang, Linwei; Huang, Shiqing; Liu, Wei; Yan, Xiaoyu; Zhang, Gang; Zhang, Zengyu; Zhao, Peng [Organic Letters, 2020]

73
ethyl 2-(3-allyl-4,6-dioxo-2-thioxotetrahydropyrimidin-1(2H)-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate [ No CAS ]
[ 1137-41-3 ]
ethyl (Z)-2-(3-allyl-5-(2-(4-benzoylphenyl)hydrazono)-4,6-dioxo-2-thioxotetrahydropyrimidin-1(2H)-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: (4-aminophenyl)(phenyl)methanone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: ethyl 2-(3-allyl-4,6-dioxo-2-thioxotetrahydropyrimidin-1(2H)-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate With pyridine at 0 - 5℃; for 2h;	General Procedure for the Synthesis of Compounds 10aand 10b General procedure: A diazonium solution was prepared by dissolving(0.02 mol) of para-toluidine or 4-aminobenzophenone in 30 mL water and 6 mL concentrated HCl; this solution wascooled to 0 °C. The solution was then treated with 0.02 molsodium nitrite in 20 mL of water, were added graduallywith stirring for 30 min with cooling in an ice bath to completethe diazotization. The formed diazonium chloridewas slowly added to compound 6 in pyridine with stirringat 0-5 °C for 2 h. The mixture was added with stirring toice-cold water. The resulting solid was filtered off, driedand recrystallized from methanol

Reference： [1]Abdel-Motaal, Marwa; Alanzy, Asmaa L.; Asem, Medhat [Acta Chimica Slovenica, 2020, vol. 67, # 2, p. 560 - 569]

74
C₁₅H₁₃NO₃ [ No CAS ]
[ 1137-41-3 ]
C₂₈H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane at 20℃; for 18h;	1-23 (Example 1-23) Synthesis of H-291 A solution of H-48 (200 mg, 0.784 mmol) and 4-aminobenzophenone (170 mg, 0.863 mmol) in dichloromethane (2 mL) was stirred at room temperature for 18 hours. After 1 M hydrochloric acid was added to the mixture, the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1) to give H-291 as a yellow oily substance (300 mg, 0.664 mmol, 85%).The measured NMR spectrum and HR-ESI-MS result of H-291 are described below. 1H NMR (400 MHz, CDCl3) δ 3.08 (1H, dd, J = 14.2, 6.8 Hz), 3.22 (1H, dd, J = 14.2, 5.5 Hz), 3.65 (3H, s), 4.92 (1H, ddd, J = 7.8, 6.8, 5.5 Hz), 6.40 (1H, d, J = 7.8 Hz), 6.59 (2H, d, J = 8.7 Hz), 7.20-7.74 (14H, m), 8.32 (1H, bs); HRESIMS calcd for C28H24N2O4Na [M+Na]+ 475.1634, found 475.1631.

Reference： [1]Current Patent Assignee: TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES - EP3680233, 2020, A1 Location in patent: Paragraph 0230-0232

75
[ 201230-82-2 ]
[ 626-62-0 ]
[ 1137-41-3 ]
N-(4-benzoylphenyl)cyclohexanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Irradiation;

Reference： [1]Connell, Timothy U.; Forni, José A.; Micic, Nenad; Polyzos, Anastasios; Weragoda, Geethika [Angewandte Chemie - International Edition, 2020, vol. 59, # 42, p. 18646 - 18654][Angew. Chem., 2020, vol. 132, # 42, p. 18805 - 18813,9]

76
[ 111-25-1 ]
[ 1137-41-3 ]
C₂₅H₃₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydride In tetrahydrofuran; ethyl acetate at -10 - 25℃; for 24h; Inert atmosphere;	1.1 (1) Weigh 1.225g (6.25mmol) of 4-aminobenzophenone, add it to a 100mL two-necked round bottom flask equipped with a stirring magnet, put a rubber stopper on one bottle and the other Connect the double-row pipes, start the vacuuming operation, and introduce nitrogen gas, these two operations are repeated 3 times. After adding 37.5mL of anhydrous tetrahydrofuran solution, mix ethyl acetate and liquid nitrogen to create a low temperature environment, keep the temperature at -10, add 0.45g (18.75mmol) of NaH, remove the ice bath device and let the temperature rise to room temperature, step by step 6.5g (37.5mmol) of C6H13Br was added dropwise and stirred at room temperature for 24h. After the reaction is completed, add ice water to react to remove excess NaH, extract with dichloromethane and water system, collect the extract in the organic phase, remove the water with saturated NaCl solution and anhydrous MgSO4, and use rotary evaporation to obtain the crude product. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether/ethyl acetate (v/v=10:1). 2.26 g (5.38 mmol) of the intermediate of formula (IV) was obtained as a yellow solid with a yield of 86%.

Reference： [1]Current Patent Assignee: BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY - CN111875522, 2020, A Location in patent: Paragraph 0027-0030

77
[ 17696-11-6 ]
[ 1137-41-3 ]
N-(4-benzoylphenyl)-8-bromooctanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 8-bromooctanoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; Stage #2: (4-aminophenyl)(phenyl)methanone With dmap; triethylamine In dichloromethane at 20℃;	4.1.34 N-(4-benzoylphenyl)-8-iodooctanamide (48) To a solution of octanoic acid (1eq, 1.12mmol, 250mg) in DCM (0.11mmol.mL-1) was added oxalyl chloride (2eq, 2.24mmol, 0.197mL) with some drops of DMF at 0°C. The resulting clear solution was stirred until completion of the reaction. The mixture was concentrated under reduced pressure and a solution of 4-amino benzophenone (1.2eq, 1.34mmol, 265mg), Et3N (2eq, 2.24mmol, 0.312mL) and DMAP (0.05eq, 0.056mmol, 7mg) in DCM (5mL) was added slowly and then stirred at room temperature. The mixture was diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (DCM/AcOEt, 50:50) to afford the N-(4-benzoylphenyl)-8-bromooctanamide as a white-yellowish solid (0.831mmol, 327mg, 74%). 1H NMR (300MHz, CDCl3): δ(ppm) 7.85-7.79 (m, 2H, 2×CHar), 7.79-7.71 (m, 2H, 2×CHar), 7.68-7.62 (m, 2H, 2×CHar), 7.62-7.53 (m, 1H, CHar), 7.53-7.44 (m, 2H, 2×CHar), 7.39 (s, 1H, NH), 3.41 (t, J=6.8Hz, 2H, CH2-Br), 2.51-2.35 (m, 2H, CH2-CONH), 1.92-1.81 (m, 2H, CH2), 1.81-1.66 (m, 2H, CH2), 1.49-1.37 (m, 6H, 3×CH2). HRMS (ESI+): calcd for C21H25NO2Br [M+H]+ m/z 402.1059; found 402.1069. NaI (2.25eq, 14.54mmol, 2.18g) was added to a solution of bromo compound previously obtained (1eq, 6.46mmol, 2.60g) in acetone (0.7mol.L-1). The solution was allowed to reflux during 2h then concentrated. The residue was solubilized in DCM and NaI/NaBr salts were filtered off. The organic layer was then concentrated under reduced pressure to afford the expected iodo compound 48 as a yellow viscous oil (6.45mmol, 2.90g, quant.). 1H NMR (300MHz, CDCl3): δ (ppm) 8.30 (s, 1H, NH), 7.81-7.72 (m, 4H, 4×CHar-CO), 7.68 (d, J=8.8Hz, 2H, 2×CHar), 7.61-7.52 (m, 1H, CHar), 7.50-7.37 (m, 2H, 2×CHar), 3.14 (t, J=7.0Hz, 2H, CH2-I), 2.38 (t, J=7.5Hz, 2H, CH2-CONH), 1.82-1.73 (m, 2H, CH2), 1.70 (m, 2H, CH2), 1.34 (m 6H, 3×CH2). 13C NMR (75MHz, CDCl3): δ (ppm) 196.1 (C=O), 172.2 (CONH), 142.5 (CIV-NHCO), 137.8 (CIV-CO), 132.7 (CIV-CO), 132.4 (CHar), 131.7 (2×CHar), 129.9 (2×CHar), 128.4 (2×CHar), 118.9 (2×CHar), 37.7 (CH2-CONH), 33.4 (CH2), 30.3 (CH2), 29.1 (CH2), 28.3 (CH2), 25.4 (CH2), 7.3 (CH2-I). HRMS (ESI+): calcd for C21H25NO2I [M+H]+ m/z 450.0922; found 450.0930.

Reference： [1]Smadja, Jimmy; Quéméner, Agnès; Maillasson, Mike; Sicard, Benoit; Leray, Aurélien; Arzel, Laurence; Lebreton, Jacques; Mortier, Erwan; Dubreuil, Didier; Mathé-Allainmat, Monique [Bioorganic and Medicinal Chemistry, 2021, vol. 39]

78
[ 69040-48-8 ]
[ 1137-41-3 ]
C₃₁H₃₅NO₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol at 60℃; for 20h;	5 Example 5: Preparation of benzophenone-2-aminopropyl diethyl methacrylate (IIIb) Add 18.4 g (0.1 mol) of hydroxyethyl methacrylate acrylate prepared in Preparation Example 1 into a 250 mL three-necked flask,Add 100mL ethanol and stir,After it is completely dissolved, add 9.85g (0.05mol) 4-aminobenzophenone,The temperature was raised to 60°C to react for 20 hours. Spin the reaction solution to dryness,It was recrystallized from ethanol and ethyl acetate to obtain 24.2 g of light yellow solid with a yield of 85%.

Reference： [1]Current Patent Assignee: JIANGSU BIOSURF BIOTECH - CN112898171, 2021, A Location in patent: Paragraph 0113-0114

79
[ 69040-48-8 ]
[ 1137-41-3 ]
C₂₂H₂₃NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In ethanol at 60℃; for 14h;	1 Example 1: Preparation of benzophenone-2-aminopropyl ethyl methacrylate (Ia) Add 18.4 g (0.1 mol) of hydroxyethyl methacrylate acrylate prepared in Preparation Example 1 into a 250 mL three-necked flask,Add 100mL ethanol and stir,After it is completely dissolved, add 19.7g (0.1mol) 4-aminobenzophenone,The temperature was raised to 60°C and reacted for 14 hours. Spin the reaction solution to dryness,Recrystallized with ethanol and ethyl acetate to obtain 34 g of light yellow solid with a yield of 90%.

Reference： [1]Current Patent Assignee: JIANGSU BIOSURF BIOTECH - CN112898171, 2021, A Location in patent: Paragraph 0105-0106

80
maleimidylethylpropenoate [ No CAS ]
[ 1137-41-3 ]
C₂₂H₂₀N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol at 65℃; for 16h;	2 Example 2: Preparation of benzophenone-2-aminopropyl ethyl maleimide (Ib) Add 19.5 g (0.1 mol) of the maleimido ethyl acrylate prepared in Preparation Example 2 into a 250 mL three-necked flask,Add 100mL ethanol and stir,After it is completely dissolved, add 19.7g (0.1mol) 4-aminobenzophenone,The temperature was raised to 65°C to react for 16 hours. Spin the reaction solution to dryness,It was recrystallized from ethanol and ethyl acetate to obtain 34.5 g of light yellow solid with a yield of 88%.

Reference： [1]Current Patent Assignee: JIANGSU BIOSURF BIOTECH - CN112898171, 2021, A Location in patent: Paragraph 0107-0108

81
[ 107947-20-6 ]
[ 1137-41-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	With N-hydroxyphthalimide; benzeneseleninic acid In dichloromethane at 80℃; for 48h; Green chemistry;	2.2 General procedure for the PhSe(O)OH/NHPI-catalyzed aerobic oxidative deoximation reactions General procedure: To a 100 mL reaction tube equipped with a piece of magnetic bar, 0.5 mmol of oxime 1, 0.075 mmol of PhSe(O)OH, 0.05 mmol of NHPI and 1 mL of DMC were subsequently added. The tube was then sealed with PTFE screw plug and magnetically stirred at 80 °C for 48 h (Safety warning: the reaction tube was made of thick glass and could endure at least 7 atmosphere pressures). After cooling to room temperature, the solvent was removed by rotatory evaporator, and the residue was subjected to flash column chromatography on silica gel (Silica gel G) to give the related carbonyl product 2 (eluent: petroleum ether/EtOAc=10:1).

Reference： [1]Wang, Feng; Yang, Chenggen; Shi, Yaocheng; Yu, Lei [Molecular catalysis, 2021, vol. 514]

82
2-(5-methyl-4,9-dioxo-1-oxa-5-azaspiro[5.5]undeca-7,10-dien-3-yl)acetaldehyde [ No CAS ]
[ 1137-41-3 ]
3-(2-((4-benzoylphenyl)amino)ethyl)-5-methyl-1-oxa-5-azaspiro[5.5]undeca-7,10-diene-4,9-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 2-(5-methyl-4,9-dioxo-1-oxa-5-azaspiro[5.5]undeca-7,10-dien-3-yl)acetaldehyde; (4-aminophenyl)(phenyl)methanone In ethanol at 0 - 20℃; Stage #2: With tetramethylammonium triacetoxyborohydride In ethanol at 0 - 20℃;	General procedure g for the synthesis of compounds 27-38. General procedure: To a stirred solution of 26 (0.010 g, 0.043 mmol) in ethanol (1 mL).The resultant mixture was cooled to 0 C, aniline (0.003 g,0.034 mmol) was added and stirred at room temperature till theconsumption of substrate, monitored by TLC. The mixture wascooled to 0 C, MeNB(OAC)H (0.068 g, 0.258 mmol) was addedportion-wise and stirred at room temperature. After completion ofstarting material the reaction mixture was quenched with ice at0 C, then extracted with ethyl acetate (2 10 mL), was dried overNa2SO4. The solvent was removed under reduced pressure, and thecrude product was purified by silica gel column chromatography toafford compound 27 respectively.

Reference： [1]Dhorma, Lama Prema; Teli, Mahesh K.; Nangunuri, Bhargav Gupta; Venkanna, Arramshetti; Ragam, Rao; Maturi, Arunkranthi; Mirzaei, Anvar; Vo, Dang-Khoa; Maeng, Han-Joo; Kim, Mi-hyun [European Journal of Medicinal Chemistry, 2022, vol. 227]

83
[ 673-22-3 ]
[ 1137-41-3 ]
(E)-(4-((2-hydroxy-4-methoxybenzylidene)amino)phenyl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol at 50℃; for 1h;	2.2. Synthesis and structural analysis HMPM was synthesized by Schiff-base reaction, performed inethanol at mild conditions (Scheme S1). Its synthetic procedures aredescribed in detail as follows. To 170 mL anhydrous ethanol solution of4-Aminobenzophenone (2.00 g, 10.1 mmol) was added 2-hydroxy-4-methoxybenzaldehyde (1.54 g, 10.1 mmol). The reaction was stirredat 50 C for 1 h, and cooled down to room temperature. The precipitatedproduct was collected via vacuum filtration using ethanol to rinse. Finalyield: 85% (2.87 g). Purity: 98% (calculated based on the integrationratio of the 1H NMR peaks). The 1H NMR peaks, coupling constant (J),together with the chemical shifts, are collected from the 1H NMR spectrum(Fig. S1) and reported as follows. 1H NMR (600 MHz, DMSO-d6) ofHMPM, (ppm): 13.34 (s, 1H), 8.95 (s, 1H), 7.82 (d, 2H, J = 8.4 Hz),7.75 (d, 2H, J = 7.2 Hz), 7.69 (t, 1H, J1 = 7.2 Hz, J2 = 14.4 Hz),7.62-7.55 (m, 3H), 7.52 (d, 2H, J = 7.8 Hz), 6.59 (d, 1H, J = 7.2 Hz),6.53 (s, 1H), 3.83 (s, 3H). The 13C NMR peaks with the correspondingchemical shifts of HMPM are collected from its 13C NMR spectrum(Fig. S2) and reported as bellow. 13C NMR (151 MHz, DMSO-d6) ofHMPM, (ppm): 197.4, 166.8, 166.6, 165.9, 154.4, 139.9, 137.0, 135.1,133.9, 132.1, 131.1, 123.9, 115.6, 109.8, 103.5, 58.1. HRMS of HMPM[M + H+]: m/z 322.1283, calcd 322.1287 (Fig. S3).

Reference： [1]Duan, Yuai; Gao, Li; Han, Hongliang; Han, Tianyu; Liu, Yang; Wei, Wei; Zhang, Xunxue [Dyes and Pigments, 2022, vol. 197]

84
[ 540-80-7 ]
[ 109-63-7 ]
[ 1137-41-3 ]
[ 98-80-6 ]
[ 2128-93-0 ]

Yield	Reaction Conditions	Operation in experiment
26 mg	Stage #1: tert.-butylnitrite; boron trifluoride diethyl ether complex; (4-aminophenyl)(phenyl)methanone In tetrahydrofuran at 0 - 20℃; for 1.5h; Stage #2: phenylboronic acid With potassium fluoride; (triphenylphosphine)gold(I) chloride; ascorbic acid In dimethyl sulfoxide; acetonitrile at 20℃; for 16h; Schlenk technique; Inert atmosphere; UV-irradiation;	Aryldiazonium Salts 1; General Procedure General procedure: To a solution of the corresponding aniline (1.0 equiv) in anhydrousTHF was added BF3·Et2O (1.4 equiv) at 0 °C. The mixture was stirredfor 30 min, then tert-butyl nitrite (1.2 equiv) was added dropwise andthe resulting suspension was allowed to warm to room temperatureover 1 h. The solvent was removed under reduced pressure and theobtained solid was washed with cold methanol and diethyl ether. Allthe aryldiazonium salts were dried using a high vacuum pump andwere stored in the dark at -20 °C.Biaryl Compounds 2; General Procedure BA Schlenk tube was charged with Ph3PAuCl, (8 mg, 0.016 mmol, 0.1equiv), the corresponding aryldiazonium salt (1.5 equiv) and the corresponding arylboronic acid (1.0 equiv). The tube was evacuated andbackfilled with nitrogen (×3). Acetonitrile (1.5 mL previously degassed by the freeze-pump-thaw method, three cycles) was added.Next, a freshly prepared solution of ascorbic acid [0.05 M in dryDMSO (0.01 equiv), 32 L] was added followed by KF (9.4 mg, 1.6mmol, 1.0 equiv). The reaction mixture was stirred at room temperature for 16 h under irradiation with blue LEDs or without irradiation.The solvent was then removed under reduced pressure and the cruderesidue was purified by column chromatography on silica gel usinghexanes or hexanes/EtOAc as the eluent.

Reference： [1]Medina-Mercado, Ignacio; Porcel, Susana [Synthesis, 2022]

85
[ 527-69-5 ]
[ 1137-41-3 ]
N-(4-benzoylphenyl)furan-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With pyridine In chloroform at 20℃;	3.2.2. general Procedure for the Preparation of 8-15 General procedure: A solution of the substituted aniline (18 mmol) in 30 mLof dry CHCl3 was added dropwise to a solution of 1 or 2 (9mmol) in 20 mL dry of CHCl3 and 3 mL of dry pyridine at -2°C. The resulting solution was stirred overnight. After completion of the reaction, 30 mL of 0.1 M NaHCO3 solution was added onto the solution with stirring, then the organic layer was separated and dried over Na2SO4, and the solvent was evaporated under reduced pressure. The product was washed with concentrated HCl (30 mL). Using the general procedure, the following compounds were synthesized

Reference： [1]Abu-Qatouseh, Luay; Idrees, Gada; Joshi, Rajendra; Khanfar, Monther; Mallah, Eyad; Mubarak, Mohammsad S.; Sweidan, Kamal; Tahir, Muhammad Nawaz [Letters in Organic Chemistry, 2022, vol. 19, # 4, p. 314 - 325]

86
[ 26726-16-9 ]
[ 1137-41-3 ]
N-(4-benzoylphenyl)-5-bromofuran-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine In chloroform at 20℃;	3.2.2. general Procedure for the Preparation of 8-15 General procedure: A solution of the substituted aniline (18 mmol) in 30 mLof dry CHCl3 was added dropwise to a solution of 1 or 2 (9mmol) in 20 mL dry of CHCl3 and 3 mL of dry pyridine at -2°C. The resulting solution was stirred overnight. After completion of the reaction, 30 mL of 0.1 M NaHCO3 solution was added onto the solution with stirring, then the organic layer was separated and dried over Na2SO4, and the solvent was evaporated under reduced pressure. The product was washed with concentrated HCl (30 mL). Using the general procedure, the following compounds were synthesized

Reference： [1]Abu-Qatouseh, Luay; Idrees, Gada; Joshi, Rajendra; Khanfar, Monther; Mallah, Eyad; Mubarak, Mohammsad S.; Sweidan, Kamal; Tahir, Muhammad Nawaz [Letters in Organic Chemistry, 2022, vol. 19, # 4, p. 314 - 325]

87
[ 1137-41-3 ]
(E)-4,4’-(1,2-diphenylethene-1,2-diyl)dianiline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.8%	With pyridine; titanium(IV) tetrachloride; zinc powder In tetrahydrofuran at 20℃; Inert atmosphere;	2.2.1. Synthesis of (E)-4,4’-(1,2-diphenylethene-1,2-diyl)dianiline (1) Into a 500 mL two-necked round-bottom flask was added 10.5 g (160mmol) of zinc dust, and 180 mL of freshly distilled THF was injectedunder nitrogen atmosphere. TiCl4 (8.8 mL, 80 mmol) was injected dropThen 10 mL of pyridine was added. The reaction mixture was refluxedfor 2.5 h. 4-Aminobenzophenone (7.9 g, 40 mmol) dissolved in 100 mLof THF was injected and the reaction mixture was refluxed overnight.After cooling to room temperature, 100 mL of K2CO3 aqueous solution(10 wt%) was added to quench the reaction. The mixture was filtered,and the filtrate was extracted with DCM. The combined organic phaseswere dried over anhydrous magnesium sulfate. After filtration and solventevaporation, the crude product was purified by a silica gel columnusing PE/EA (20:1, by volume) as eluent. A yellow solid was obtained in33.8% yield (2.45 g). 1H NMR (300 MHz, DMSO-d6), (TMS, ppm): 7.09(m, 6H), 6.98 (d, 4H), 6.52 (d, 4H), 6.26 (d, 4H), 5.04 (s, 4H). 13C NMR(150 MHz, DMSO-d6), (ppm): 146.85, 144.95, 138.64, 131.71, 131.25,130.97, 127.58, 125.78, 113.21.

Reference： [1]Li, Hongkun; Li, Yongfang; Shi, Fengyun; Yang, Yonggang; Zhou, Ziqing [Dyes and Pigments, 2022, vol. 203]

88
[ 1502-00-7 ]
[ 1137-41-3 ]
N-(4-benzoylphenyl)adamantane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With trifluorormethanesulfonic acid; potassium iodide In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere;

Reference： [1]Chen, Tieqiao; Huang, Tianzeng; Liu, Long; Szostak, Michal; Wang, Qun; Zuo, Dongxu [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	1137-41-3	MDL No. :	MFCD00007895
Formula :	C₁₃H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RBKHNGHPZZZJCI-UHFFFAOYSA-N
M.W :	197.23	Pubchem ID :	14346
Synonyms :

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	60.72
TPSA :	43.09 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.56 cm/s

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	2.74
Log Po/w (WLOGP) :	2.51
Log Po/w (MLOGP) :	2.34
Log Po/w (SILICOS-IT) :	2.68
Consensus Log Po/w :	2.41

[ CAS No. 1137-41-3 ] {[proInfo.proName]}

Quality Control of [ 1137-41-3 ]

Related Doc. of [ 1137-41-3 ]

Product Details of [ 1137-41-3 ]

Calculated chemistry of [ 1137-41-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1137-41-3 ]

Application In Synthesis of [ 1137-41-3 ]

[ 1137-41-3 ] Synthesis Path-Upstream 1~2

[ 1137-41-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 1137-41-3 ]

Aryls

Ketones

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.25
Solubility :	0.111 mg/ml ; 0.000564 mol/l
Class :	Soluble
Log S (Ali) :	-3.3
Solubility :	0.099 mg/ml ; 0.000502 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.51
Solubility :	0.00612 mg/ml ; 0.000031 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.2

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1137-41-3 ] {[proInfo.proName]}

Quality Control of [ 1137-41-3 ]

Related Doc. of [ 1137-41-3 ]

Product Details of [ 1137-41-3 ]

Calculated chemistry of [ 1137-41-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1137-41-3 ]

Application In Synthesis of [ 1137-41-3 ]

[ 1137-41-3 ] Synthesis Path-Upstream 1~2

[ 1137-41-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1137-41-3 ]

Aryls

Ketones

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1137-41-3 ]