Name: 5703-26-4|2-(4-Methoxyphenyl)acetaldehyde|95%
Brand: Ambeed
SKU: A129505
Rating: 96 (22 reviews)

1
[ 637-69-4 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Pyridine-2,6-dicarboxylic acid; iron(II) tetrafluoroborate hexahydrate; iodosylbenzene In chloroform at 20℃; for 20h; Molecular sieve; regioselective reaction;
85%	With ammonium persulfate; Pd(E-2-(benzylthio)-N-{(2-methoxynaphthalene-1-yl)methylene}benzenamine)Cl; 1-butyl-3-methylimidazolium Tetrafluoroborate In water at 70℃; for 0.25h; Microwave irradiation; regioselective reaction;	Microwave assisted palladium complex catalyzed selectiveoxidation of terminal olefin to aldehyde General procedure: To a homogeneous solution of Pd(II) complex (0.5 mol%) in 10 ml[bmim]BF4eH2O (2:1), substituted styrene (1 mmol) was added,followed by ammonium persulfate (1.5 mmol) as oxidant weretaken in glass tubes, sealed and placed in the cavity of microwaveapparatus. Then set parameters are as follows: microwave irradiationpower 80W, increasing time 5 min, target temperature 70 C,standing time 15 min, standing temperature 70 C. A maximumirradiation power of 80Wand 70 C were applied for 15 min. Afterthe temperature reached 70 C, the instrument was automaticallyadjusted to maintain a constant temperature. After completion of the reaction (monitored through TLC), the reaction mixture wascooled to room temperature then diluted with 2 10 ml water,then extracted with ethyl acetate and dried over Na2SO4. Theresulting solution was concentrated under vacuum. Product wasfurther purified by chromatographic separation with a mixture ofethyl acetate:hexane (1:10)
48%	With iodosylbenzene In acetonitrile at 25℃;

	With diethyl ether; iodine; mercury(II) oxide
	(i) Tl(NO₃)3*3H₂O, MeOH, (ii) aq. H₂SO₄; Multistep reaction;
99 % Spectr.	With 2,6-dichloropyridine N-oxide In chloroform-d1 at 25℃; for 0.5h;
	Multi-step reaction with 2 steps 1: lead (IV)-acetate 2: sodium acetate; methanol
	Multi-step reaction with 2 steps 1: lead (IV)-acetate
99 %Spectr.	With [Ru(tmttp)O₂]; oxygen In chloroform-d1 at 60℃; for 5h;
99 %Spectr.	With 2,6-dichloropyridine N-oxide; dichlororuthenium(IV) meso-tetrakis(2,6-dichlorophenyl)porphyrin In chloroform-d1 at 25℃;
64 %Spectr.	With {tetrakis(2,6-dichlorophenyl)porphyrinato}iron(III) triflate; iodosylbenzene In dichloromethane at 20℃; for 6h; Inert atmosphere;
55 %Chromat.	With chloro[5,10,15,20-tetrakis(4-dimethylamino-2,3,5,6-tetrafluorophenyl)porphyrinate]iron(III); dihydrogen peroxide; silver trifluoromethanesulfonate In 1,4-dioxane; water at 20℃; chemoselective reaction;
	Multi-step reaction with 2 steps 1: oxygen; styrene monooxygenase / Enzymatic reaction 2: styrene oxide isomerase / Enzymatic reaction

Reference： [1]Chowdhury, Abhishek Dutta; Ray, Ritwika; Lahiri, Goutam Kumar [Chemical Communications, 2012, vol. 48, # 44, p. 5497 - 5499]
[2]Sarma, Kuladip; Devi, Namita; Sutradhar, Dipankar; Sarma, Bipul; Chandra, Asit K.; Barman, Pranjit [Journal of Organometallic Chemistry, 2016, vol. 822, p. 20 - 28]
[3]Srinivasan, K.; Michaud, P.; Kochi, J. K. [Journal of the American Chemical Society, 1986, vol. 108, # 9, p. 2309 - 2320]
[4]Mannich; Jacobsohn [Chemische Berichte, 1910, vol. 43, p. 193]
[5]Tiffeneau [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1902, vol. 134, p. 1507][Annales de Chimie (Cachan, France), 1907, vol. <8> 10, p. 360]
[6]McKillop,A. et al. [Journal of the American Chemical Society, 1973, vol. 95, p. 3635 - 3640]
[7]Chen, Jian; Che, Chi-Ming [Angewandte Chemie - International Edition, 2004, vol. 43, # 37, p. 4950 - 4954]
[8]Criegee et al. [Chemische Berichte, 1957, vol. 90, p. 1070,1080]
[9]Criegee et al. [Chemische Berichte, 1957, vol. 90, p. 1070,1080]
[10]Jiang, Gaoxi; Chen, Jian; Thu, Hung-Yat; Huang, Jie-Sheng; Zhu, Nianyong; Che, Chi-Ming [Angewandte Chemie - International Edition, 2008, vol. 47, # 35, p. 6638 - 6642]
[11]Location in patent: scheme or table Hu, Wen-Xiang; Li, Pei-Rong; Jiang, Gaoxi; Che, Chi-Ming; Chen, Jian [Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3190 - 3194]
[12]Chen, Guo-Qiang; Xu, Zhen-Jiang; Zhou, Cong-Ying; Che, Chi-Ming [Chemical Communications, 2011, vol. 47, # 39, p. 10963 - 10965]
[13]Du, Yi-Dan; Tse, Chun-Wai; Xu, Zhen-Jiang; Liu, Yungen; Che, Chi-Ming [Chemical Communications, 2014, vol. 50, # 84, p. 12669 - 12672]
[14]Wu, Shuke; Liu, Ji; Li, Zhi [ACS Catalysis, 2017, vol. 7, # 8, p. 5225 - 5233]

2
[ 5703-26-4 ]
[ 3353-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	ueber das Natriumhydrogensulfit-Addukt;
	With pyridine; hydroxylamine hydrochloride In ethanol Heating;
	With hydroxylamine hydrochloride; sodium carbonate In methanol; water at 20℃; for 3h; optical yield given as %de;

With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;

Aldoximes; General Procedure General procedure: To a solution of the aldehyde in CH2Cl2 (0.2 M) was added hydroxylamine hydrochloride (2.0 equiv) and Et3N (4.2 equiv) and the mixture was stirred at r.t. for 16 h. The reaction was quenched with sat. aq NaHCO3 and extracted with CH2Cl2. The combined organic layers were washed with aq 1 M HCl, dried (MgSO4), and concentrated to give the crude aldoxime, which was purified by flash chromatography. The known aldoximes 1,18 4a,5i 4b,19 4c,20 4d,18 4e,21 4f,22 4g,18 4h,23 4i,244j,20 7,25 10a,25 10b,26 10c,18 10d,27 10e,27 10f,28 10j,5i and 1929 were synthesized following the general procedure described above.

Reference： [1]Baerwald,L. [Diss. <Frankfurt 1936> S. 23]
[2]Yuasa, Yoshifumi; Shibuya, Shiroshi; Yuasa, Yoko [Synthetic Communications, 2003, vol. 33, # 22, p. 3947 - 3952]
[3]Location in patent: experimental part Castellano, Sabrina; Kuck, Dirk; Viviano, Monica; Yoo, Jakyung; López-Vallejo, Fabian; Conti, Paola; Tamborini, Lucia; Pinto, Andrea; Medina-Franco, José L.; Sbardella, Gianluca [Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7663 - 7677]
[4]Keita, Massaba; Vandamme, Mathilde; Paquin, Jean-François [Synthesis, 2015, vol. 47, # 23, p. 3758 - 3766]

3
[ 110-91-8 ]
[ 5703-26-4 ]
[ 80743-36-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	In chloroform at 20℃; for 3h; Molecular sieve;	General procedure for Diels-Alder reaction between methyl coumalate with phenylacetaldehyde enamines General procedure: Step 1: To a solution of 2-(4-methoxyphenyl)acetaldehyde (300 mg, 2.0 mmol, 1.0 equiv.) in 10 mL of dry chloroform at R.T., 4Å molecular sieves (1 gram, activated at 160°C for 48 hours) was added, followed by adding morpholine (348 mg, 4.0 mmol, 2.0 equiv.) in one portion. The solution was stirred at R.T. for 3 hours (monitored by the crude 1H NMR) and filtered. After being concentrated, the solid was washed with dry hexane and decant to give the corresponding enamine as a white solid (420 mg, 96 % yield), which was used directly for the next step. 1H NMR (400 MHz, Chloroform-d) δ = 7.13 (d, J=8.4, 2H), 6.80 (d, J=8.2, 2H), 6.48 (d, J=14.2, 1H), 5.43 (d, J=14.2, 1H), 3.81 - 3.74 (m, 7H), 3.04 - 2.96 (m, 4H).
86%	In benzene Heating;
	In chloroform at 20℃; for 5h; Molecular sieve; Schlenk technique;

Reference： [1]Yu, Huangchao; Kraus, George A. [Tetrahedron Letters, 2018, vol. 59, # 45, p. 4008 - 4010]
[2]Crispi, Giuseppe; Giacconi, Paola; Rossi, Elisabetta; Stradi, Riccardo [Synthesis, 1982, # 9, p. 787 - 788]
[3]Wu, Rongpei; Gao, Ke [Organic and Biomolecular Chemistry, 2021, vol. 19, # 18, p. 4032 - 4036]

4
[ 2933-29-1 ]
[ 5703-26-4 ]
2-p-methoxybenzylidenamino-4,5,6,7-tetrahydrobenzothiazole [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1988,vol. 65,p. 429 - 431

5
[ 6388-72-3 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium tetrahydroborate In benzene at 45℃; for 2.5h;
90%	With indium(III) chloride In tetrahydrofuran at 25℃; for 0.166667h;
90%	With oxovanadium(V) ethoxydichloride In ethanol at 20℃; for 4h;

89%	With gold(III) chloride; silver hexafluoroantimonate In 1,4-dioxane at 20℃; for 0.166667h; regioselective reaction;	Representive procedure for the rearrangement of 1a General procedure: To a solution of the epoxide 1a (100 mg, 0.61 mmol) in dry dioxane (3 mL) freshly prepared AuCl3 (0.2 mg, 0.1 mol %) and AgSbF6 (0.6 mg, 0.3 mol %) solutions in dry dioxane were added and the reaction mixture was allowed to stir at room temperature. The reaction was monitored by TLC and found to complete in 20 min. Dioxane was evaporated. The residue was loaded on a silica gel column and was eluted with EtOAc/hexanes (7/93) mixtures to obtain pure compound 2a in 83% yield as colorless liquid.
80%	With silica gel In ethyl acetate for 0.5h; Ambient temperature;
66%	at 240℃; for 5h; other aryloxiranes;
66%	at 240℃; for 5h;
52%	With glass wool at 300℃; Gas phase; Inert atmosphere; Flow reactor; regioselective reaction;
23%Spectr.	With carbon monoxide; C₂₉H₃₂IrN₅O; bis(trifluoromethane)sulfonimide lithium In benzene-d6 at 80℃; for 24h; Schlenk technique; chemoselective reaction;

Reference： [1]Shaozu, Wu; Yulan, Zhang; Huidong, Wang [Gazzetta Chimica Italiana, 1991, vol. 121, # 11, p. 519 - 520]
[2]Ranu, Brindaban C.; Jana, Umasish [Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8212 - 8216]
[3]Martinez, Fernando; Campo, Carmen del; Llama, Emilio F. [Journal of the Chemical Society. Perkin transactions I, 2000, # 11, p. 1749 - 1752]
[4]Gudla, Vanajakshi; Balamurugan, Rengarajan [Tetrahedron Letters, 2012, vol. 53, # 39, p. 5243 - 5247]
[5]Lemini; Ordonez; Perez-Flores; Cruz-Almanza [Synthetic Communications, 1995, vol. 25, # 18, p. 2695 - 2702]
[6]Haridas, K.; Dev, Sukh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1018 - 1020]
[7]Haridas, K.; Dev, Sukh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1018 - 1020]
[8]Ramaswamy, Govindarajan K.; Somasundaram, Angalan; Kuppuswamy, Balasubramanian K.; Velayudham, Murugesan [Journal of the Chinese Chemical Society, 2013, vol. 60, # 1, p. 97 - 102]
[9]Maulbetsch, Theo; Jürgens, Eva; Kunz, Doris [Chemistry - A European Journal, 2020, vol. 26, # 46, p. 10634 - 10640]

6
[ 23786-14-3 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With diisobutylaluminium hydride; In toluene; at -78℃; for 1.16667 - 1.25h;	Example 4 2-R (AMINOCARBONYL) AMINOL-5- (4-METHOXYPHENYL)-N-F (3S)-PIPERIDIN-3-YLLTHIOPHENE-3- carboxamide (4-METHOXY-PHENYL)-ACETALDEHYDE. To a stirred solution of (4-METHOXY-PHENYL)-ACETIC acid methyl ester (18.0 g, 100 mmol) in anhydrous toluene (200 RNL) cooled to-78 C under N2 was added diisobutylaluminum hydride (DIBAL, 1.0 M in toluene, 150 mL, 150 mmol) over a period of 10-15 minutes. The mixture was stirred AT-78 C for an additional 2h. The reaction was quenched by the slow addition OF MEOH, followed by the introduction of 10% Rochelle's Salt. The suspension was diluted with EtOAc and stirred at room temperature for LH. The EtOAc layer was set aside and the aqueous layer was extracted with EtOAc (2x). The combined organic layers were combined and dried over NA2S04 and filtered. The solution was concentrated under vacuum to yield 12.0 g (100%) of the title aldehyde as a yellow viscous semisolid, which was used in the next step without purification. LC/MS (APCI, ES, M+H=151).
80%	With diisobutylaluminium hydride; In dichloromethane; toluene; at -78℃; for 1.5h;Inert atmosphere;	(4-Methoxyphenyl)acetic acid (13) (30.30 g, 182.3 mmol) in concd H2SO4 (15.2 mL, 273.5 mmol) and MeOH (100 mL) was heated at reflux for 5 h. The light yellow solution was cooled to r.t., diluted with H2O (400 mL), and extracted with C6H6 (4 × 150 mL). The combined organic phases were washed with H2O (200 mL), 5% aq NaHCO3 (200mL), and H2O (200 mL). The solvents were removed by rotary evaporation, and the residue was distilled to give methyl (4-methoxyphenyl)acetate (29.35 g, 89%) as a colorless liquid; bp 98-102 C/1 torr(Lit.11b 116-117 C/2.5 torr).DIBAL-H in CH2Cl2 (1.0 M; 5.96 mL, 5.96 mmol) was transferred by syringe to a solution of methyl (4-methoxyphenyl)acetate (1.024 g, 5.68mmol) in PhMe (20 mL) at -78 C. After stirring for 1.5 h, the reaction mixture was quenched by the addition of aq HCl (1 N; 4 mL). The cloudy white mixture was stirred at -78 C for 15 min, allowed to warm to r.t. over 15 min, diluted with aq HCl (1 N; 20 mL), and extracted with Et2O (4 × 40 mL). The combined organic phases were washed with sat. aq NaHCO3 (40 mL) and dried over MgSO4. Removal of the solvents by rotary evaporation, followed by distillation of the residue, furnished 14 (686.4 mg, 80%) as a clear liquid; bp (Kugelrohr,1.8 torr) 150 C (Lit.11c 110-115 C/1 torr).

Reference： [1]Patent: WO2005/16909,2005,A1 .Location in patent: Page/Page column 66
[2]Journal fur Praktische Chemie - Chemiker-Zeitung,1996,vol. 338,p. 706 - 710
[3]Synthesis,2018,vol. 50,p. 1053 - 1089
[4]Journal of the American Chemical Society,1977,vol. 99,p. 3059 - 3067
[5]Synthesis,2011,p. 2935 - 2940
[6]Angewandte Chemie - International Edition,2013,vol. 52,p. 8045 - 8049
Angew. Chem.,2013,vol. 125,p. 8203 - 8207
[7]Angewandte Chemie - International Edition,2015,vol. 54,p. 11240 - 11244
Angew. Chem.,2015,vol. 127,p. 11392 - 11396,5

7
[ 702-23-8 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	2.B.72.1 Example 72 Preparation of Intermediate 72 Step 1: To a solution of 4-methoxyphenethyl alcohol (1.52 g, 10.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added Dess-Martin reagent (4.45 g, 10.5 mmol) in one portion. The formed mixture was allowed to warm to the ambient temperature for 1 hour. Washed with sat. Na2S2O3 (aq) and 1M NaOH, brine respectively. Dried over MgSO4, filtered, and concentrated in vacuo to give 1.50 g (100%) of the desired aldehyde as a viscous oil. This product was used as crude without any further purification.
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	41.1 To a solution of 4-methoxyphenethyl alcohol (1.52 g, 10.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added Dess-Martin reagent (4.45 g, 10.5 mmol) in one portion. The formed mixture was allowed to warm to the ambient temperature for 1 h. Washed with sat. Na2S2O3 (aq) and 1M NaOH, brine respectively. Dried over MgSO4, evaporated in vacuo to give 1.50 g (100%) of the desired aldehyde as a viscous oil. This product was used as crude without any further purification.
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	B.III.3.1 Example 3: Preparation of Compound 3.; Step 1: To a solution of 4-methoxyphenethyl alcohol (1.52 g, 10.0 mmol) inCHzCI2 (50 mL) at0 C was added Dess-Martin reagent (4.45 g, 10.5 mmol) in one portion. The formed mixture was allowed to warm to the ambient temperature for1 h. Washed with sat. Na2S203 (aq) and 1M NaOH, brine respectively. Dried overMgS04, evaporated in vacuo to give 1.50 g (100%) of the desired aldehyde as a viscous oil. This product was used as crude without any further purification.

100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	41.1 Step 1: To a solution of 4-methoxyphenethyl alcohol (1.52 g, 10.0 mmol) in CH2Cl2 (50 mL) at 00 C was added Dess-Martin reagent (4.45 g, 10.5 mmol) in one portion. The formed mixture was allowed to warm to the ambient temperature for 1 h. Washed with sat. Na2S2O3 (aq) and 1M NaOH, brine respectively. Dried over MgSO4, evaporated in vacuo to give 1.50 g (100%) of the desired aldehyde as a viscous oil. This product was used as crude without any further purification.
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2h;	99.c c) 2-(4-methoxyphenyl)acetaldehyde (I-55) c) 2-(4-methoxyphenyl)acetaldehyde (I-55) [0300] Dess-Martin periodinane (5.8 g; 13.79 mmol; 1.05 eq) was added to a solution of 2-(4-methoxyphenyl)ethan-1-ol (2 g; 13.14 mmol; 1 eq) in dichloromethane (90 mL) at 0°C. The reaction mixture was stirred at 0°C for 30 minutes and at room temperature for 1.5 hours. Dichloromethane (100 mL) was added and the organic layer was washed with sodium thiosulfate 10% in water (100 mL) and sodium hydroxide 1M (100 mL), dried over sodium sulfate, filtrated and concentrated to dryness. The title compound, 2-(4-methoxyphenyl)acetaldehyde was obtained in quantitative yield (2.1 g) as a colorless oil. 1H NMR (CDCl3): δ 3.68 (s, 2H), 3.87 (s, 3H), 6.97 (d, 2H), 7.19 (d, 2H), 9.78 (s, 1H).
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2h;	99.c c) 2- (4-methox yphen yl) acetaldeh yde (1-55) c) 2- (4-methox yphen yl) acetaldeh yde (1-55) Dess-Martin periodinane (5.8 g; 13.79 mmol; 1.05 eq) was added to a solution of 2- (4-methoxyphenyl)ethan- l-ol (2 g; 13.14 mmol; 1 eq) in dichloromethane (90 mL) at 0°C. The reaction mixture was stirred at 0°C for 30 minutes and at room temperature for 1.5 hours. Dichloromethane (100 mL) was added and the organic layer was washed with sodium thiosulfate 10% in water (100 mL) and sodium hydroxide 1M (100 mL), dried over sodium sulfate, filtrated and concentrated to dryness. The title compound, 2-(4-methoxyphenyl)acetaldehyde was obtained in quantitative yield (2.1 g) as a colorless oil. 1H NMR (CDC13): δ 3.68 (s, 2H), 3.87 (s, 3H), 6.97 (d, 2H), 7.19 (d, 2H), 9.78 (s, 1H).
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	41.1 To a solution of 4-methoxyphenethyl alcohol (1.52 g, 10.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added Dess-Martin reagent (4.45 g, 10.5 mmol) in one portion. The formed mixture was allowed to warm to the ambient temperature for 1 h. Washed with sat. Na2S2O3 (aq) and 1M NaOH, brine respectively. Dried over MgSO4, evaporated in vacuo to give 1.50 g (100%) of the desired aldehyde as a viscous oil. This product was used as crude without any further purification.
100%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	41.1 To a solution of 4-methoxyphenethyl alcohol (1.52 g, 10.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added Dess-Martin reagent (4.45 g, 10.5 mmol) in one portion. The formed mixture was allowed to warm to the ambient temperature for 1 h. Washed with sat. Na2S2O3 (aq) and 1M NaOH, brine respectively. Dried over MgSO4, evaporated in vacuo to give 1.50 g (100%) of the desired aldehyde as a viscous oil. This product was used as crude without any further purification.
95%	With 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; Sodium hydrogenocarbonate In lithium hydroxide monohydrate; propan-2-one at 20℃; for 6h;
95%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1.25h;
90%	With Dess-Martin periodane In dichloromethane at 20℃; for 2h; Inert atmosphere;
88%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 2h;
86%	With tert.-butylnitrite; 9-azanoradamantane-N-oxyl In acetonitrile at 20℃; for 9h; chemoselective reaction;
85%	With Dess-Martin periodane In dichloromethane for 2h; Reflux;	7 4.1.7 2-(4-Methoxyphenyl)acetaldehyde 2-(4-Methoxyphenyl)ethan-1-ol (300µL, 2mmol) was dissolved in 139 CH2Cl2 (30mL). Dess-Matin 140 periodinane (975mg, 2.25mmol) was added and the resulting reaction mixture was refluxed for 2 h. The solvents were removed under reduced pressure, and subjected to flash column chromatography to give the 141 product 2-(4-methoxyphenyl)acetaldehyde (250mg, 85%). 1H NMR (300MHz, CDCl3) δ=9.69 (t, J=2.4Hz, 1H), 7.13-7.09 (m, 2H), 6.92-6.87 (m, 2H), 3.78 (s, 3H), 3.60 (d, J=2.4Hz, 2H)ppm. 13C NMR (75MHz, CDCl3) δ=199.51, 158.82, 130.53, 123.61, 114.29, 55.09, 49.50ppm.
84%	With pivaloyl chloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; for 1h;
82.4%	With 2-iodoxybenzoic acid In acetonitrile at 80℃; for 2h; Inert atmosphere;
79%	Stage #1: 2-(4-Methoxyphenyl)ethanol With bis(trichloromethyl) carbonate; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h; Stage #2: With triethylamine at -78 - 20℃; for 0.166667h;
75%	With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 4h;
75%	With pyridinium chlorochromate In dichloromethane at 20℃; for 4h; cooling;
75%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile for 3h; Reflux;	Oxidation of 4-methoxyphenylethanol with 2-iodoxybenzoic acid (IBX) 4-Methoxyphenylethanol (0.34 g, 2.24 mmol) was dissolved in acetonitrile (50 mL), then IBX (3.72 g, 6mmol) was added and the solution was refluxed for 3 h. The mixture was cooled to r.t, filtered (Celite) andthe filtrate was evaporated. The residue was purified by column chromatography (10:1 n-pentane/ethylacetate) to give pure 4-methoxyphenylacetaldehyde (0.25 g, 75% yield), identical (H-NMR, ES-MS) to anauthentic sample.
66%	With pyridine-SO₃ complex; triethylamine In dichloromethane; dimethyl sulfoxide for 8h;	126.1 Example 126 . l-{6-[4-(2-dimethylamino-ethoxy)-phenyl] -5-ethyl-2-thiophen-2-yl-thieno[2,3-d]pyrimidin-4-ylamino}-3-inethyl-pyrrole-2,5-d ione hydrochloride; Step 1. Preparation of (4-methoxy-phenylVacetaldehyde; 4-methoxyphenethylalcohol (2g, 13.14mmol) and triethylamine (7.33ml,52.56mmol) were dissolved in dichloromethane (50ml). Therein, the solution of pyridine sulfide complex (4.18g, 26.28mmol) in dimethylsulfoxide (10ml) was added, and the reaction mixture was stirred for 8 hours. The solvent was removed under reduced pressure. The residue was purified by column chromatography (n-hexane: ethyl acetate = 3:1) to give 1.29g (yield: 66.0%, yellow oil) of the target compound.[1218] 1H-NMR (400D, CDCI) δ 10.03(t, IH, J=2.0Hz), 7.12(d, 2H, J=8.4Hz), 6.86(d, 2H,J=6.4Hz), 3.79(s, 3H), 3.62(d, 2H, J=2.0Hz)
57%	With Dess-Martin periodane In dichloromethane at 20℃; for 1.5h;
55%	With Dess-Martin periodane In dichloromethane at 20℃; for 18h;
53%	With sulphur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine In dichloromethane; dimethyl sulfoxide at -15℃; for 0.5h; Inert atmosphere;
50%	With mesoporous silica; pyridinium chlorochromate In dichloromethane at 20℃; for 2h;
49%	With Dess-Martin periodane In dichloromethane at 0 - 25℃; for 4h;
44.4%	Stage #1: 2-(4-Methoxyphenyl)ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -70℃; for 0.333333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -70 - 20℃; for 1h;	20.A [0334] Step A: DMSO (5.2 mL, 72.6 mmol) in dichloromethane (14.5 mL) was added to a solution of oxalyl chloride (3.1 mL, 36.3 mmol) in dichloromethane (83 mL) at -70 °C under nitrogen. After stirring for 5 minutes, 2-(4-methoxyphenyl) ethanol (5.0 g, 33.0 mmol) dissolved in dichloromethane (33 mL) was added drop wise (20 min). Stirring was continued for an additional 20 min. and triethyl amine (9.7mL, 69.3 mmol) was added, and the reaction mixture was stirred and warmed slowly to room temperature for 1 hour. The reaction mixture was diluted with water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide 2-(4- methoxyphenyl)acetaldehyde (553) (2.2 g, 44.4%) as an oil residue.
44.4%	Stage #1: 2-(4-Methoxyphenyl)ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -70℃; for 0.666667h; Stage #2: With triethylamine In dichloromethane at -70 - 20℃; for 1h;	20.A 0326] Step A: DMSO (5.2 niL, 72.6 mmol) in dichloromethane (14.5 niL) was added to a solution of oxalyl chloride (3.1 rnL, 36.3 mmol) in dichloromethane (83 mL) at -70 0C under nitrogen. After stirring for 5 minutes, 2-(4-methoxyphenyl) ethanol (5.0 g, 33.0 mmol) dissolved in dichloromethane (33 mL) was added drop wise (20 min). Stirring was continued for an additional 20 min. and triethyl amine (9.7mL, 69.3 mmol) was added, and the reaction mixture was stirred and warmed slowly to room temperature for 1 hour. The reaction mixture was diluted with water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide 2-(4- methoxyphenyl)acetaldehyde (553) (2.2 g, 44.4%) as an oil residue.
37%	With N-chloro-succinimide; N-tert-butylbenzenesulfinamide; potassium carbonate In dichloromethane at 0℃; for 2h; Schlenk technique; Molecular sieve; Inert atmosphere;
34%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;	91.1 A solution of 4-methoxyphenyl ethanol (15.0 g, 98.2 mmol) in 150 mL of methylene chloride was stirred at 0° C. while Dess-Martin periodinane (50 g, 1.2 eq.) was added in small portions. The ice-bath was removed and the reaction was stirred at rt for 1 h. The reaction mixture was then diluted with methylene chloride (100 mL), washed with 10% sodium thiosulfate, saturated NaHCO3 solution, water, saturated NaCl solution, and dried over Na2SO4. The product was purified using silica gel chromatography (100% hexanes to 20% EtOAC/hexanes) to afford 5.3 g (34%) of 4-methoxyphenyl acetaldehyde. A suspension of glyoxalic acid hydrate (2.45 g, 26.6 mmol) and morpholine hydrochloride (3.28 g, 26.35 mmol) in dioxane (25 mL) was stirred as water (2 mL) was added. The homogeneous solution and 4-methoxyphenyl acetaldehyde (3.8 g, 25.3 mmol) was then added and the solution was stirred at reflux for 24 h. The solvent was evaporated and a solid was formed after addition of 20 mL of water. The solid was collected and washed with water to give 5.1 g (98%) of the product: MS m/z 189 (M-17+H).
34%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;
29%	With 1H-imidazole; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 1h;
	With chromium trioxide-pyridine complex In dichloromethane
	With bis(trichloromethyl) carbonate In dimethyl sulfoxide
	With Annogen In hydrogenchloride at 35℃; ΔH(excit.), ΔE(excit.), ΔS(excit.), ΔG(excit.).;
	With Annogen In hydrogenchloride at 29.9 - 44.9℃; for 24h; effect of the temperature;
	With hydrogenchloride; chloramine-T at 29.9 - 44.9℃; for 24h; activation parameters: ΔH(excit.), ΔS(excit.), ΔG(excit.), and E_a;
	With hydrogenchloride; N-bromo-p-toluenesulfonamide; anhydrous sodium perchlorate In methanol; lithium hydroxide monohydrate at 35℃;
	With hydrogenchloride; chloramine-T In lithium hydroxide monohydrate at 34.85℃;
	With N-tert-butylbenzenesulfinimidoyl chloride; zinc oxide In dichloromethane at 0℃; for 0.5h;
	With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane cooling;
	With Collins reagent In dichloromethane at 25℃;
	With pyridinium chlorochromate In dichloromethane for 3h; cooling;
	With Dess-Martin periodane In dichloromethane at 20℃;
	With Collins reagent In dichloromethane at 25℃;
	With Sodium hydrogenocarbonate; Dess-Martin periodane In dichloromethane at 20℃; for 1h;	(4-Methoxy-phenyl)-acetaldehyde; Dess-Martin periodinane (3.2 g, 7.29 mmol, 1.1 equiv) is added in one portion to a mixture of 4-methoxyphenethyl alcohol (1.0 g, 6.63 mmol) and NaHC03 (1. 1 g, 13.2 mmol, 2.0 equiv) in CH2CI2, under an argon atmosphere. The resulting mixture is stirred for 1 h at RT and directly loaded on a silica gel (60 g) column. Flash chromatography purification (CH2CI2/Et2O, 95/5), affords the title compound as a colorless oil : ES-MS: 148.9 [M-H]- ; single peak at tR= 6.12 min (System 1); Rf = 0.74 (CH2CI2/Et2O, 95/5)
	With Dess-Martin periodane In dichloromethane at 20℃; Inert atmosphere;	General procedure for the synthesis of aromatic and aliphatic acetaldehydes: General procedure: The alcohol (1.0 eq) was added to a suspension of Dess-Martin periodinane (1.2 eq) in CH2Cl2(100 mM) under an argon atmosphere at room temperature. The mixture was allowed to stir for0.5 - 20 hours, while consumption of starting material was monitored by TLC. After the reactionwas complete, 1M Na2S2O3 (equal volume to CH2Cl2) was added. After stirring for 15 minutes,the phases were separated and the aqueous phase was extracted with CH2Cl2 twice. Thecombined organic layers were washed with 5% NaHCO3 and brine, and dried over Na2SO4. Thesolvent was evaporated under reduced pressure and the residue was purified by columnchromatography to afford analytically pure aldehydes.b) alcohol precursors for aldehydes 13, 14, 20 (solid alcohols)The alcohol (1.0 eq) was dissolved in CH2Cl2 (200 mM) and the solution was added to asuspension of Dess-Martin periodinane (1.2 eq) in CH2Cl2 (200 mM) under an argon atmosphereat room temperature. The mixture was allowed to stir for 0.5 - 20 hours (TLC monitoring). Then,Et2O (equal volume to CH2Cl2), 1M Na2S2O3 and saturated NaHCO3 (both equal volume toCH2Cl2) were added. After stirring for 15 minutes, the phases were separated and the aqueousphase was extracted with Et2O twice. The combined organic layers were washed with sat.NaHCO3 and brine, and dried over Na2SO4. The solvent was evaporated under reduced pressureand the residue was purified by column chromatography to afford analytically pure aldehydes.
	With pyridinium chlorochromate In dichloromethane
185 mg	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 80℃; for 3h;	41.A A. To a solution of 4-methoxyphenethyl alcohol (184 mg, 1.21 mmol) in EtOAc (24 mL) was added 2-iodoxybenzoic acid (1 .02 g, 3.64 mmol), and the mixture was heated to 80°C open to air for 3 h. The mixture was cooled to 0°C for 10 mm then filtered through Celite and concentrated to give Compound No. 80 (185 mg) as ayellow oil.
	With Dess-Martin periodane In dichloromethane at 0℃; for 0.25h;
	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; Inert atmosphere;
708 mg	With Dess-Martin periodane In dichloromethane at 0 - 20℃; Inert atmosphere;
	With Sodium hydrogenocarbonate; Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
	With Sodium hydrogenocarbonate In dichloromethane at 20℃; for 3h; Dean-Stark; Inert atmosphere;
	With Dess-Martin periodane
	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 2.5h; Inert atmosphere;
	With Dess-Martin periodane In dichloromethane for 1h;
	With Sodium hydrogenocarbonate; Dess-Martin periodane In dichloromethane at 20℃; for 2h; Inert atmosphere;

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[6]Current Patent Assignee: VALNEVA SE - WO2013/171281, 2013, A1 Location in patent: Page/Page column 150
[7]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/107623, 2008, A1 Location in patent: Page/Page column 47
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/107624, 2008, A1 Location in patent: Page/Page column 49
[9]De Luca, Lidia; Giacomelli, Giampaolo; Masala, Simonetta; Porcheddu, Andrea [Journal of Organic Chemistry, 2003, vol. 68, # 12, p. 4999 - 5001]
[10]O'Brien, Connor J.; Droege, Daniel G.; Jiu, Alexander Y.; Gandhi, Shivaani S.; Paras, Nick A.; Olson, Steven H.; Conrad, Jay [Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 8926 - 8935]
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8
[ 104-01-8 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With borane-THF; Dess-Martin periodane 1.) THF, 4 h, 2.) CH₂Cl₂, 1 h; Yield given; Multistep reaction;
70 % Spectr.	With hydrogen; 2,2-dimethylpropanoic anhydride In tetrahydrofuran at 80℃; for 24h;
	Multi-step reaction with 2 steps 1: 98 percent / oxalyl chloride / benzene / 3 h / Ambient temperature 2: 48 percent / CdCl₂*1.5 DMF, NaBH₄, HMPA / acetonitrile / 0.05 h / -5 °C

	Multi-step reaction with 2 steps 2: Na2(OCH₂CH₂OMe)2>
	Multi-step reaction with 3 steps 1: sulfuric acid / 3 h / Reflux 2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 2 h / 80 °C
	With polyphosphoric acid at 100℃;
	Multi-step reaction with 3 steps 1: sulfuric acid / 6.5 h / Inert atmosphere; Reflux 2: diisobutylaluminium hydride; hydrogenchloride / tetrahydrofuran; hexane; water / 0 - 20 °C / pH 1 / Inert atmosphere 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux; Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: oxalyl dichloride / benzene / 3.5 h / 20 °C 2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N,N-dimethyl-formamide; cadmium(II) chloride / acetonitrile / 0.67 h / -5 - 0 °C 2.2: pH 3
	Stage #1: 4-Methoxyphenylacetic acid With iron(III) chloride; potassium borohydride; water; calcium carbonate at 55℃; for 3h; Stage #2: With hydrogenchloride; manganese(IV) oxide for 4h;	1.1; 2.1; 3.1; 4.1 Example 4: (1) Preparation of 4-methoxyphenylacetaldehyde Dissolve 30.09g of calcium carbonate in 700g of water.Add 100g of 4-methoxyphenylacetic acid,After stirring for 50 minutes to completely dissolve the solid,35.71 g of potassium borohydride and 5.86 g of ferric chloride were added.Raise the temperature to 55 ° C for 3 h,After the consumption of 4-methoxyphenylacetic acid by TLC,Neutralize the reaction solution with 15% hydrochloric acid to pH=7.Add 62.78g of active manganese dioxide and continue the reaction for 4h.After the reaction was completed, the reaction solution was cooled to room temperature.Adjust the pH to 8~9 with 1mol/L sodium hydroxide solution.Add 700g of dichloromethane and stir for 1h.The mixture was allowed to stand for separation, and the organic phase was dried over anhydrous sodium sulfate.Filtration gave a solution of 4-methoxyphenylacetaldehyde.

Reference： [1]Kraus, George A.; Melekhov, Alex [Journal of Organic Chemistry, 1999, vol. 64, # 2-5, p. 1720 - 1722]
[2]Nagayama; Shimizu; Yamamoto [Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 10, p. 1803 - 1815]
[3]Motsios; Ahmar; Nadi; Paris [Synthetic Communications, 1991, vol. 21, # 6, p. 819 - 826]
[4]Lambert,J.B. et al. [Journal of the American Chemical Society, 1977, vol. 99, # 9, p. 3059 - 3067]
[5]Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]
[6]Ahmad, Imran; Pathak, Vinay; Vasudev, Prema G.; Maurya, Hardesh K.; Gupta, Atul [RSC Advances, 2014, vol. 4, # 47, p. 24619 - 24634]
[7]Kondoh, Azusa; Odaira, Kenta; Terada, Masahiro [Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11240 - 11244][Angew. Chem., 2015, vol. 127, p. 11392 - 11396]
[8]Aechtner, Tobias; Barry, David A.; David, Ellen; Ghellamallah, Cédric; Harvey, Daniel F.; De La Houpliere, Alix; Knopp, Monika; Malaska, Michael J.; Pérez, Dolores; Schärer, Kaspar A.; Siesel, Brian A.; Vollhardt, K. Peter C.; Zitterbart, Robert [Synthesis, 2018, vol. 50, # 5, p. 1053 - 1089]
[9]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - WO2007/102679, 2007, A1
[10]Current Patent Assignee: ZHUHAI BERI PHARMACEUTICAL TECH - CN110156684, 2019, A Location in patent: Paragraph 0027-0029; 0034-0036; 0041-0043; 0048-0050

9
[ 5703-26-4 ]
[ 74-88-4 ]
[ 32454-14-1 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 2406 - 2407

10
[ 5703-26-4 ]
[ 536-74-3 ]
[ 857282-86-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h;
80%	Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran; hexane at 20℃; for 2h;

Reference： [1]Zhang, Xiaoxia; Sarkar, Sampa; Larock, Richard C. [Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 236 - 243]
[2]Zhang, Xiaoxia; Larock, Richard C. [Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12230 - 12231]

11
N-fluorenylmethoxycarbonyl-3-amino-3-[(1R,2R,3S,4R)-3-O-methyl-1,2-O-isopropylidenefuranos-4-yl]propanoic acid [ No CAS ]
[ 5703-26-4 ]
[ 126727-04-6 ]
[ 3173-56-6 ]
2-{3-Benzyl-1-[2-(4-methoxy-phenyl)-ethyl]-ureido}-N-[2-carbamoyl-1-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-3-phenyl-propionamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2004,vol. 13,p. 687 - 706

12
N-fluorenylmethoxycarbonyl-3-amino-3-[(1R,2R,3S,4R)-3-O-benzyl-1,2-O-isopropylidenefuranos-4-yl]propanoic acid [ No CAS ]
[ 5703-26-4 ]
[ 126727-04-6 ]
[ 3173-56-6 ]
2-{3-Benzyl-1-[2-(4-methoxy-phenyl)-ethyl]-ureido}-N-[1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-carbamoyl-ethyl]-3-phenyl-propionamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2004,vol. 13,p. 687 - 706

13
[ 5703-26-4 ]
[ 298-12-4 ]
[ 184376-10-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With morpholin hydrochloride In 1,4-dioxane; water for 24h; Heating / reflux;	91.1 A solution of 4-methoxyphenyl ethanol (15.0 g, 98.2 mmol) in 150 mL of methylene chloride was stirred at 0° C. while Dess-Martin periodinane (50 g, 1.2 eq.) was added in small portions. The ice-bath was removed and the reaction was stirred at rt for 1 h. The reaction mixture was then diluted with methylene chloride (100 mL), washed with 10% sodium thiosulfate, saturated NaHCO3 solution, water, saturated NaCl solution, and dried over Na2SO4. The product was purified using silica gel chromatography (100% hexanes to 20% EtOAC/hexanes) to afford 5.3 g (34%) of 4-methoxyphenyl acetaldehyde. A suspension of glyoxalic acid hydrate (2.45 g, 26.6 mmol) and morpholine hydrochloride (3.28 g, 26.35 mmol) in dioxane (25 mL) was stirred as water (2 mL) was added. The homogeneous solution and 4-methoxyphenyl acetaldehyde (3.8 g, 25.3 mmol) was then added and the solution was stirred at reflux for 24 h. The solvent was evaporated and a solid was formed after addition of 20 mL of water. The solid was collected and washed with water to give 5.1 g (98%) of the product: MS m/z 189 (M-17+H).
98%	With water; morpholin hydrochloride In 1,4-dioxane for 24h; Reflux;

Reference： [1]Current Patent Assignee: ALTO NEUROSCIENCE - US2008/27041, 2008, A1 Location in patent: Page/Page column 65-66
[2]Location in patent: experimental part Tao, Ming; Aimone, Lisa D.; Huang, Zeqi; Mathiasen, Joanne; Raddatz, Rita; Lyons, Jacquelyn; Hudkins, Robert L. [Journal of Medicinal Chemistry, 2012, vol. 55, # 1, p. 414 - 423]

14
[ 5703-26-4 ]
[ 39878-65-4 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11295 - 11308

15
[ 5703-26-4 ]
[ 32136-81-5 ]

Reference： [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1996,vol. 338,p. 706 - 710

16
[ 1123-49-5 ]
[ 5703-26-4 ]
[ 630421-51-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With piperidine In ethanol for 12h; Heating / reflux;	2.B.72.2 Step 2: A solution of 3,5-dimethyl-4-nitro-isoxazole (142 mg, 1.0 mmol), 4-methoxy-phenylacetaldehyde from Example 3, Step 1 (180 mg, 1.1 mmol) in piperidine (0.1 mL) and ethanol (2 mL) was heated to reflux for 12 hours ours After cooling down to the ambient temperature, the product precipitated out was collected by filtration. The cake was washed with cold ethanol thoroughly to afford 130 mg (51%) of the desired product as a grayish solid. 1H NMR (CDCl3) δ 2.88 (s, 3H), 3.87 (s, 3H), 7.02 (d, J=8.5 Hz, 2H), 7.50 (d, J=9.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.81 (d, J=8.5 Hz, 2H); MS m/z 257 (M++H).
51%	With piperidine In ethanol for 12h; Heating / reflux;	B.III.3.2 Step 2: A solution of 3, 5-dimethyl-4-nitro-isoxazole (142 mg, 1.0 mmol), 4-methoxyphenylacetaldehyde from Example 3, Step 1 (180 mg,1.1 mmol) in piperidine(0. 1 mL) and ethanol (2 mL) was heated to reflux for 12 h. After cooling down to the ambient temperature, the product precipitated out was collected by filtration. The cake was washed with cold ethanol thoroughly to afford 130 mg(51%) of the desired product as a grayish solid. 'H NMR(CDC13)8 2.88 (s, 3H), 3.87 (s, 3H), 7.02 (d, J=8. 5 Hz, 2H), 7.50 (d, J=9. 0 Hz, 1H), 7.57 (d, J=9. 0 Hz, 1H), 7.81 (d, J=8. 5 Hz, 2H); LC-MS (retention time: 1.24 min, method B), MSm/z 257 (M++H).
51%	With piperidine In ethanol for 12h; Heating / reflux;	41.2 Step 2: A solution of 3,5-dimethyl-4-nitro-isoxazole (142 mg, 1.0 mmol), 4-methoxy-phenylacetaldehyde from Example 3, Step 1 (180 mg, 1.1 mmol) in piperidine (0.1 mL) and ethanol (2 mL) was heated to reflux for 12 h. After cooling down to the ambient temperature, the product precipitated out was collected by filtration. The cake was washed with cold ethanol thoroughly to afford 130 mg (51%) of the desired product as a grayish solid. 1H NMR (CDCl3) δ 2.88 (s, 3H), 3.87 (s, 3H), 7.02 (d, J=8.5 Hz, 2H), 7.50 (d, J=9.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.81 (d, J=8.5 Hz, 2H); MS m/z 257 (M++H).

51%	With piperidine In ethanol for 12h; Heating / reflux;	41.2 A solution of 3,5-dimethyl-4-nitro-isoxazole (142 mg, 1.0 mmol), 4-methoxy-phenylacetaldehyde from Example 3, Step 1 (180 mg, 1.1 mmol) in piperidine (0.1 mL) and ethanol (2 mL) was heated to reflux for 12 h. After cooling down to the ambient temperature, the product precipitated out was collected by filtration. The cake was washed with cold ethanol thoroughly to afford 130 mg (51%) of the desired product as a grayish solid.1H NMR (CDCl3) δ 2.88 (s, 3H), 3.87 (s, 3H), 7.02 (d, J=8.5 Hz, 2H), 7.50 (d, J=9.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.81 (d, J=8.5 Hz, 2H); MS m/z 257 (M++H).
51%	With piperidine In ethanol for 12h; Heating / reflux;	41.2 A solution of 3,5-dimethyl-4-nitro-isoxazole (142 mg, 1.0 mmol), 4-methoxy-phenylacetaldehyde from Example 3, Step 1 (180 mg, 1.1 mmol) in piperidine (0.1 mL) and ethanol (2 mL) was heated to reflux for 12 h. After cooling down to the ambient temperature, the product precipitated out was collected by filtration. The cake was washed with cold ethanol thoroughly to afford 130 mg (51%) of the desired product as a grayish solid. 1H NMR (CDCl3) δ 2.88 (s, 3H), 3.87 (s, 3H), 7.02 (d, J=8.5 Hz, 2H), 7.50 (d, J=9.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.81 (d, J=8.5 Hz, 2H); MS m/z 257 (M++H). Step 3: This product was prepared by the same procedure as described in Example 39, Step 2. 1H NMR (CDCl3) δ 2.70 (s, 3H), 3.87 (s, 3H), 7.00-7.03 (m, 2H), 7.84 (s, 1H), 7.96-7.98 (m, 2H); MS m/z 275, 277 (M++H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2006/183694, 2006, A1 Location in patent: Page/Page column 64-65
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2003/99274, 2003, A1 Location in patent: Page 79-80
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/99825, 2007, A1 Location in patent: Page/Page column 51
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/107623, 2008, A1 Location in patent: Page/Page column 47
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/107624, 2008, A1 Location in patent: Page/Page column 49

17
[ 5703-26-4 ]
[ 1001-55-4 ]
[ 845889-04-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sulfur; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃;	4 2-AMINO-5- (4-METHOXY-PHENYL)-THIOPHENE-3-CARBOXYLIC acid methyl ester. To a solution of 4- methoxyphenylacetaldehyde (12. 0g) in DMF (200ML) was added cyanomethyl acetate (8.9 mL, 100 mmol) and sulfur (3.2g, 100mmol), followed by diisopropylethylamine (Hunig's Base, 17.4 mL, 100 mmol). The resultant suspension immediately turned dark yellow to brown with an exotherm. The reaction mixture was stirred overnight at room temperature. The reaction was slowly added to water (~1L) while stirring. A tan precipitate formed and was filtered after an additional 30 minutes of stirring. The resultant solid was purified by column chromatography (SIO2, 10-20% ETOAC/HEXANES) TO YIELD 15.3 G (58%) OF THE TITLE COMPOUND AS A LIGHT YELLOW SOLID.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; JANETKA JAMES WALTER - WO2005/16909, 2005, A1 Location in patent: Page/Page column 66

18
[ 60-29-7 ]
[ 23786-14-3 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With diisobutylaluminium hydride; sodium hydrogencarbonate In toluene	2 (4-Methoxyphenyl)ethanal Preparation 2 (4-Methoxyphenyl)ethanal To a stirred solution of methyl 4-methoxyphenylacetate (45.0 g) in toluene (250 ml) cooled to -78° C., add a 1.5M solution of DIBALH in toluene (167 ml) over 5 h, maintaining the reaction temperature at -78° C. Stir for an additional 0.5 h, then pour into 1:1 ice/1M HCl (1500 ml) and Et2 O (500 ml). Stir the slurry for 1 h, separate the layers and extract the aq. layer with Et2 O (2*500 ml). Wash the combined organic layers with sat'd NaHCO3 (500 ml) and sat'd NaCl, dry (MgSO4), filter and evaporate to give an oil. Perform bulb-to-bulb distillation (100°-130° C., 1 mmHg) to obtain the title compound (33.9 g, 90%) as a colorless liquid. 1 H Nmr (CDCl3) δ9.71 (1H, t, J=2.4 Hz), 7.12 (2H, m), 6.89 (2H, m), 3.79 (3H, s) 3.61 (2H, m).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5476847, 1995, A

19
[ 32454-14-1 ]
[ 104-47-2 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
		(i) 4-Methoxyphenylacetaldehyde (Compound 74) This compound was prepared from 4-methoxyphenylacetnitrile in the same manner of Compound 45. 1 H-NMR (270 MHz) (CDCl3) 9.72 (t, 1H, J=2.6 Hz), 7.13 (d, 2H, J=8.8 Hz), 6.91 (d, 2H, J=8.8 Hz), 3.81 (s, 3H), 3.63 (d, 2H, J=2.6 Hz) ppm.

Reference： [1]Patent: US5789423,1998,A

20
[ 5703-26-4 ]
[ 105-56-6 ]
[ 949527-44-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃; for 0.333333h;	5.3. General procedure for the synthesis of 2-aminothiophenes3ge3i General procedure: A mixture of ethyl cyanoacetate (13.6 mmol), sulfur (13.6 mmol) and triethylamine (13.6 mmol) in dimethylformamide (DMF; 15 mL) was stirred at 50 C. A solution of the corresponding aldehyde (13.6 mmol) in DMF (10 mL)was added dropwise over 20 min. The mixture then was stirred at 50 C overnight. The reaction mixture was cooled, poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer was separated, washed with brine, and dried over Na2SO4 then concentrated under reduced pressure. The title compound was obtained by column chromatography (EtOAc: hexane 1: 15). 5.3.1. Ethyl 2-amino-5-(4-methoxyphenyl)lthiophene-3-carboxylate(3g) The parameters for 3g were: pale yellow solid, 60% yield, 1HNMR (400 MHz, CDCl3): d 7.37 (d, J 8.8 Hz, 2H), 7.01 (s, 1H), 6.87(d, J 8.8 Hz, 2H), 5.95 (br, 2H), 4.29 (q, J 6.8 Hz, 2H), 3.81 (s, 3H),1.37 (t, J 6.8 Hz, 3H).
60%	With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃; for 28h;	54.3 Step 3. Preparation of 2-amino-5-(4-methoxy-phenyl)-thiophen-3-carboxyric acid ethyl ester; The compound (498mg, 3.316mmol) prepared in the step 2, ethyl cyanoacetate(0.353ml, 3.316mmol) and sulfur (106mg, 3.316mmol) were dissolved in N,N-dimethylformamide (3ml). Therein, triethylamine (0.254ml, 1.824mmol) was added slowly, and the reaction mixture was stirred at 5O0C for 28 hours. After reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. Combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane: ethyl acetate = 10:1) to give 550mg (yield: 60%, pale yellow solid) of the target compound.[757] 1U NMR(400D, CDCI): δ 7.37(d, J=8.8Hz, 2H), 7.01(s, IH), 6.87(d, J=8.8Hz, 2H),5.95(br, 2H), 4.29(q, J=6.8Hz, 2H), 3.81(s, 3H), 1.37(t, J=6.8Hz, 3H)
50%	With morpholine; sulfur In ethanol at 70℃; for 0.333333h; Microwave irradiation;

Reference： [1]Kim, Hyuntae; Lee, Chulho; Yang, Jee Sun; Choi, Seonghwi; Park, Chun-Ho; Kang, Jong Soon; Oh, Soo Jin; Yun, Jieun; Kim, Myung-Hwa; Han, Gyoonhee [European Journal of Medicinal Chemistry, 2016, vol. 120, p. 74 - 85]
[2]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - WO2007/102679, 2007, A1 Location in patent: Page/Page column 69
[3]Location in patent: experimental part Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]

21
[ 5703-26-4 ]
[ 925-90-6 ]
[ 110661-90-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 4-Methoxyphenylacetaldehyde; ethylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 4h; Stage #2: With water; ammonium chloride In tetrahydrofuran	126.2 Step 2. Preparation of l-(4-methoxy-phenylVbutan-2-ol; The compound (1.29g, 7.15mmol) prepared in the step 1 was dissolved in THF(20ml). Thereafter, the temperature was lowered into -1O0C and therein, l.OM ethyl- magnesiumbromide in THF (8ml, 8.0mmol) was added, and the reaction mixture was stirred at room temperature for 4 hours. Thereafter, the reaction mixture was poured into ammonium chloride solution to quench. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography(n-hexane: ethyl acetate = 3:1) to give 1.02g (yield: 66%, yellow oil) of the target compound. [1223] 1U NMR(400D, CDCI); δ 7.12(d, 2H, J=8.4Hz), 6.86(d, 2H, J=6.4Hz), 3.79(s, 3H),3.62(s, 2H), 3.40(m, IH), 2.47 (q, 2H, J=7.2Hz), 1.00(t, 3H, J=7.2Hz)

Reference： [1]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - WO2007/102679, 2007, A1 Location in patent: Page/Page column 112-113

22
[ 5703-26-4 ]
[ 181225-39-8 ]
[ 1164114-75-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: ((5-bromo-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane) With n-butyllithium In tetrahydrofuran at -78 - -40℃; Inert atmosphere; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
75%	Stage #1: ((5-bromo-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane) With n-butyllithium In tetrahydrofuran; hexane at -78 - -40℃; Inert atmosphere; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;

Reference： [1]Nicolaou, K. C.; Robert Wu, T.; Kang, Qiang; Chen, David Y.-K. [Angewandte Chemie - International Edition, 2009, vol. 48, # 19, p. 3440 - 3443]
[2]Nicolaou; Kang, Qiang; Wu, T. Robert; Lim, Chek Shik; Chen, David Y.-K. [Journal of the American Chemical Society, 2010, vol. 132, # 21, p. 7540 - 7548]

23
[ 5703-26-4 ]
[ 137-07-5 ]
[ 33429-12-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With iron(III) chloride hexahydrate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 12h;	General procedure for the preparation of 2-benzoyl benzothiazoles (4): To 1 mL of [bmim]BF4 were added 2-aminothiophenol (1 mmol), phenylacetaldehyde (1 mmol) and FeCl3·6H2O (0.1 mmol). The reaction mixture was stirred at 80 °C for the time period as shown in Table 2. Upon completion, the mixture was cooled to room temperature and extracted with ethyl ether (5 mL × 3). The combined organic phases were concentrated under vacuum. The crude product was purified by column chromatography eluting with ethyl acetate/hexane (1-10%) to give the desired product 4.

Reference： [1]Location in patent: experimental part Fan, Xuesen; He, Yan; Wang, Yangyang; Xue, Zaikun; Zhang, Xinying; Wang, Jianji [Tetrahedron Letters, 2011, vol. 52, # 8, p. 899 - 902]

24
[ 5703-26-4 ]
[ 23451-96-9 ]
[ 1268700-07-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With iron(III) chloride hexahydrate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 12h;	General procedure for the preparation of 2-benzoyl benzothiazoles (4): To 1 mL of [bmim]BF4 were added 2-aminothiophenol (1 mmol), phenylacetaldehyde (1 mmol) and FeCl3·6H2O (0.1 mmol). The reaction mixture was stirred at 80 °C for the time period as shown in Table 2. Upon completion, the mixture was cooled to room temperature and extracted with ethyl ether (5 mL × 3). The combined organic phases were concentrated under vacuum. The crude product was purified by column chromatography eluting with ethyl acetate/hexane (1-10%) to give the desired product 4.

Reference： [1]Location in patent: experimental part Fan, Xuesen; He, Yan; Wang, Yangyang; Xue, Zaikun; Zhang, Xinying; Wang, Jianji [Tetrahedron Letters, 2011, vol. 52, # 8, p. 899 - 902]

25
[ 109-80-8 ]
[ 5703-26-4 ]
[ 74447-45-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; Molecular sieve;	4.1.17. 1-(1,3-Dioxolan-2-yl)-2-(4-methoxyphenyl)ethanone (18) This compound was prepared from methoxyacetaldehyde in 4 sequential steps in total 63% yield as follows: To a solution of 2-(4-methoxyphenyl)acetaldehyde 20 (1.000 g, 6.66 mmol), 4 Å MS (6.000 g), and 1,3-propanedithiol (0.8 mL, 7.98 mol) in anhydrous CH2Cl2 (20.0 mL) under Argon at 0 °C, boron trifluoride ethyl etherate (3.3 mL, 26.6 mmol) was added. The reaction mixture was stirred for 2 h at 0 °C, and then was allowed to warm to room temperature and stirred for 12 h. The reaction mixture was quenched by NaHCO3(aq), filtered, and extracted with CH2Cl2 (10 mL×3). The combined organic layer was dried over MgSO4 and evaporated under reduced pressure to dryness. The crude was purified by column chromatography (EA/hexane=1:8) to give 2-(4-methoxybenzyl)-1,3-dithiane 21 as a yellow-green solid (1.487 g, 93%).To a solution of 2-(4-methoxybenzyl)-1,3-dithiane 21 (1.000 g, 4.16 mmol) in anhydrous THF (10 mL) at -20 °C, n-butyllithium (2.5 M, 1.7 mL, 4.25 mmol) was added. After 30 min, anhydrous DMF (1.6 mL, 20.8 mol) was added, and the reaction mixture was allowed to warm to room temperature and stirred for 6 h. The reaction was quenched by 10% HCl(aq) (30 mL), then extracted with EA (20 mL×3). The combined organic layers were dried over MgSO4 and evaporated under reduced pressure to dryness. The crude product was purified by column chromatography (EA/hexane=1:8) to give 2-(4-methoxybenzyl)-1,3-dithiane-2-carbaldehyde 22 as a colorless oil (0.970 g, 86%).To a solution of 2-(4-methoxybenzyl)-1,3-dithiane-2-carbaldehyde 22 (1.000 g, 3.73 mmol) in toluene (20 mL), ethylene glycol (1.0 mL, 17.9 mmol) and p-toluenesulfonic acid (6 mg, 1 mol %) were added. The reaction mixture was refluxed for 12 h under Dean-Stark conditions. The reaction was cooled to room temperature, quenched by NaHCO3(aq), and extracted with EA (20 mL×3). The combined organic layers were dried over MgSO4 and evaporated under reduced pressure to dryness. The crude was purified by column chromatography (EA/hexane=1:8) to give 2-(2-(4-methoxybenzyl)-1,3-dithian-2-yl)-1,3-dioxolane 23 as a colorless oil (1.094 g, 94%).To a solution of 2-(2-(4-methoxybenzyl)-1,3-dithian-2-yl)-1,3-dioxolane (1.000 g, 3.20 mmol) in the mixed solvent of acetonitrile (100 mL) and water (35 mL) were added N-chlorosuccimide (2.128 g, 16.0 mmol) and silver nitrate (2.718 g, 16.0 mmol). The reaction solution was stirred for 5 min then quenched by Na2SO3(aq) (40 mL), NaHCO3 (aq) (40 mL), and NaCl (aq) (40 mL), filtered, and extracted with EA (100 mL×3). The combined organic layers were dried over MgSO4 and evaporated under reduced pressure to dryness. The crude was purified by column chromatography (EA/hexane=1:5) to give 1-(1,3-dioxolan-2-yl)-2-(4-methoxyphenyl)ethanone 18 as a colorless oil (1.094 g, 84%).
91%	With boron trifluoride diethyl etherate In dichloromethane; water at 0 - 20℃; for 14h; Molecular sieve; Inert atmosphere;

Reference： [1]Location in patent: experimental part Phakhodee, Wong; Toyoda, Mitsuko; Chou, Chun-Ming; Khunnawutmanotham, Nisachon; Isobe, Minoru [Tetrahedron, 2011, vol. 67, # 6, p. 1150 - 1157]
[2]Chou, Chun-Ming; Tung, Yu-Wen; Lin, Meng-I; Chan, Diana; Phakhodee, Wong; Isobe, Minoru [Heterocycles, 2012, vol. 86, # 2, p. 1323 - 1339]

26
[ 14001-64-0 ]
[ 5703-26-4 ]
2-thiomethyl-4,6-bis(4-methoxystyryl)pyrimidine [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2009,vol. 4,p. 668 - 680

27
[ 5703-26-4 ]
[ 1338349-59-9 ]
[ 144-62-7 ]
[ 1338349-57-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 4-Methoxyphenylacetaldehyde; N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide oxalate With sodium acetate; sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 15h; Stage #2: oxalic acid In diethyl ether	5.1.27. N-[2-Ethyl-2-(4-fluorophenyl)butyl]-1-(3-phenylpropyl)piperidine-4-carboxamide oxalate (20e) (Method A) To an ice-cooled mixture of N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide oxalate (0.50 g, 1.26 mmol) and hydrocinnamaldehyde (0.21 g, 1.57 mmol) in CH2Cl2 (5.0 ml) was added sodium triacetoxyborohydride (0.54 g, 2.55 mmol) and the mixture was stirred at room temperature for 15 h. The reaction mixture was concentrated in vacuo and the resulting residue was partitioned between saturated aqueous sodium bicarbonate solution and CHCl3. The organic layer was dried over Na2SO4 and evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel (MeOH/CHCl3 = 5/95) to give N-[2-ethyl-2-(4-fluorophenyl)butyl]-1-(3-phenylpropyl)piperidine-4-carboxamide (0.48 g) as a colorless oil. The compound was converted to its oxalate by treating it with oxalic acid (0.10 g, 1.11 mmol). The crude salt was suspended with CH3CN and filtered to give the title compound 20e (0.45 g, 77%) as a colorless powder.Comment1H NMR (DMSO-d6) δ: 0.60 (6H, t, J = 8.0 Hz), 1.61 (4H, q, J = 8.0 Hz), 1.65-1.75 (4H, m), 1.85-1.98 (2H, m), 2.35-2.45 (1H, m), 2.61 (2H, t, J = 7.6 Hz), 2.75 (2H, br s), 2.88-3.00 (2H, m), 3.28-3.44 (4H, m), 7.11 (2H, dd, J = 8.4, 8.8 Hz), 7.18-7.33 (7H, m), 7.48 (1H, t, J = 6.0 Hz). MS (FAB) m/z: 425 (M++1). Anal. Calcd for C27H37N2OF·C2H2O4·0.3H2O: C, 66.98; H, 7.68; N, 5.39; F, 3.65. Found: C, 66.99; H, 7.65; N, 5.29; F, 3.62.

Reference： [1]Location in patent: experimental part Watanuki, Susumu; Matsuura, Keisuke; Tomura, Yuichi; Okada, Minoru; Okazaki, Toshio; Ohta, Mitsuaki; Tsukamoto, Shin-Ichi [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5628 - 5638]

28
[ 5703-26-4 ]
[ 1338466-39-9 ]
[ 1353942-33-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 4-Methoxyphenylacetaldehyde; di-tert-butyl 1-(6-methoxypyridin-3-yl)hydrazine-1,2-dicarboxylate With hydrogenchloride In 1,4-dioxane at 80℃; for 18h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water regioselective reaction;	General procedure for copper-catalyzed pyrrolo-heterocycle synthesis from boronic acids General procedure: 6-Methoxypyridin-3-ylboronic acid (115 mg, 0.75 mmol), di-tert-butylazodicarboxylate ‘DBAD’ (115 mg, 0.5 mmol) and Cu(II)OAc-H2O (5.1 mg, 0.025 mmol) were combined in 3 mL MeOH in a 20 mL scintillation vial and heated for 1 h at 65 °C. The mixture was cooled to room temperature and 2-phenylacetaldehyde (90 mg, 0.75 mmol) was added followed by addition of 2 mL 4 N HCl in dioxane and the mixture was placed in an 80 °C heating block for 18 h. The reaction was cooled to room temperature and volatiles were removed in vacuo to give a crude oil which was partitioned between 25 mL of satd aq NaHCO3 and 100 mL CH2Cl2. Organics were extracted, dried (MgSO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography though silica gel using ethyl acetate in heptanes to elute providing 78 mg (70%) of 5-methoxy-3-phenyl-1H-pyrrolo[3,2-b]pyridine (Table 1, entry 1a) as a yellow solid.

Reference： [1]Beveridge, Ramsay E.; Gerstenberger, Brian S. [Tetrahedron Letters, 2012, vol. 53, # 5, p. 564 - 569]

29
[ 5703-26-4 ]
[ 95-54-5 ]
[ 5021-46-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With oxygen; triethylamine In toluene at 60℃; for 12h;	4.1. 2-Phenylquinoxaline (3aa) Typical procedure: Mix Et3N (2.53 mg, 0.025 mmol), 2-phenylacetaldehyde 1a (30 mg, 0.25 mmol), benzene-1,2-diamine 2a (32.4 mg, 0.3 mmol), in toluene (2.5 mL) under O2 (1 atm). The reaction mixture was stirred at 60 °C for 12 h. After cooling down to room temperature and concentrating in vacuum, the residue was purified by flash chromatography on a short silica gel (eluent: petroleum ether/ethyl acetate=20:1) to afford 47 mg (91%) of 3aa.
81%	With potassium carbonate In toluene at 90℃; for 10h; Sealed tube;

Reference： [1]Zhang, Chun; Xu, Zejun; Zhang, Liangren; Jiao, Ning [Tetrahedron, 2012, vol. 68, # 26, p. 5258 - 5262]
[2]Song, Jinli; Li, Xiaolong; Chen, Yongxin; Zhao, Mingming; Dou, Yani; Chen, Baohua [Synlett, 2012, vol. 23, # 16, p. 2416 - 2420]

30
[ 582-22-9 ]
[ 5703-26-4 ]
[ 1428269-35-5 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 11367 - 11370
Angew. Chem.,

31
[ 5703-26-4 ]
[ 56069-39-7 ]
[ 1431696-15-9 ]

Yield	Reaction Conditions	Operation in experiment
73%		General procedure: asolution of <strong>[56069-39-7]diethyl ((phenylsulfonyl)methyl)phosphonate</strong> (500mg, 1.7 mmol, 1equiv)in dry tetrahydrofuran (2 mL)was added dropwise to astirring suspension of sodium hydride (39mg, 1.53 mmol, 0.9 equiv)in dry tetrahydrofuran (5mL) at 0 C under inert condition. After 30 min, asolution of a-substituted acetaldehyde (1.7mmol, 1.0 equiv)in dry tetrahydrofuran (3mL)was added to the reaction mixture. Stirring was continued for an hour. The reaction was quenched by an addition of 5mL of sodium bisulfate (5wt %solution).The solution was concentrated under vacuum, diluted with water (10mL),and extracted with ethylacetate (3 5 mL).The combined organic extracts were washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered,and concentrated under vacuum. Purificationby flash column chromatography (silicagel; 97:3 hexane/ethylacetate)provided the desired product.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2717 - 2721

32
[ 5703-26-4 ]
[ 56069-39-7 ]
[ 863310-91-2 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: asolution of <strong>[56069-39-7]diethyl ((phenylsulfonyl)methyl)phosphonate</strong> (500mg, 1.7 mmol, 1equiv)in dry tetrahydrofuran (2 mL)was added dropwise to astirring suspension of sodium hydride (39mg, 1.53 mmol, 0.9 equiv)in dry tetrahydrofuran (5mL) at 0 C under inert condition. After 30 min, asolution of a-substituted acetaldehyde (1.7mmol, 1.0 equiv)in dry tetrahydrofuran (3mL)was added to the reaction mixture. Stirring was continued for an hour. The reaction was quenched by an addition of 5mL of sodium bisulfate (5wt %solution).The solution was concentrated under vacuum, diluted with water (10mL),and extracted with ethylacetate (3 5 mL).The combined organic extracts were washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered,and concentrated under vacuum. Purificationby flash column chromatography (silicagel; 97:3 hexane/ethylacetate)provided the desired product.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2717 - 2721

33
[ 5703-26-4 ]
[ 66416-72-6 ]
[ 1417524-82-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 80℃; for 20h; Sealed tube; regioselective reaction;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 μL, 0.5 mmol) 2a, (DMEDA) (3 μL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 °C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua [Synlett, 2013, vol. 24, # 17, p. 2315 - 2319]

34
[ 5703-26-4 ]
[ 615-43-0 ]
[ 5021-46-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 80℃; for 20h; Sealed tube; regioselective reaction;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 μL, 0.5 mmol) 2a, (DMEDA) (3 μL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 °C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua [Synlett, 2013, vol. 24, # 17, p. 2315 - 2319]

35
[ 5703-26-4 ]
[ 117832-17-4 ]
2-(2-fluoro-4-methoxyphenyl)-6,7-dimethylquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 80℃; for 20h;Sealed tube;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Synlett,2013,vol. 24,p. 2315 - 2319

36
[ 755031-80-2 ]
[ 5703-26-4 ]
6-chloro-2-(4-methoxyphenyl)-7-methylquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 80℃; for 20h; Sealed tube; regioselective reaction;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 μL, 0.5 mmol) 2a, (DMEDA) (3 μL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 °C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua [Synlett, 2013, vol. 24, # 17, p. 2315 - 2319]

37
[ 5703-26-4 ]
[ 163444-17-5 ]
2-(4-methoxyphenyl)-7-(trifluoromethyl)quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 80℃; for 20h; Sealed tube; regioselective reaction;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 μL, 0.5 mmol) 2a, (DMEDA) (3 μL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 °C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua [Synlett, 2013, vol. 24, # 17, p. 2315 - 2319]

38
[ 5703-26-4 ]
[ 63069-48-7 ]
[ 1417524-80-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 80℃; for 20h; Sealed tube; regioselective reaction;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 μL, 0.5 mmol) 2a, (DMEDA) (3 μL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 °C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua [Synlett, 2013, vol. 24, # 17, p. 2315 - 2319]

39
[ 5703-26-4 ]
[ 77087-60-6 ]
methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl)ethyl]amino}propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;	99.d d) Methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl) ethyl]amino)propanoate (I-56) d) Methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl) ethyl]amino)propanoate (I-56) [0302] Sodium triacetoxyborohydride (2.21 g; 10.43 mmol; 1.1 eq) was added to a solution of 2-(4-methoxyphenyl)acetaldehyde (I-55) (1.28 g; 8.53 mmol; 0.9 eq) and methyl 2-amino-3-[(tert-butoxy)carbonyl]amino}propanoate (I-57) (2.07 g; 9.48 mmol; 1 eq) in dichloromethane (135 mL). The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium hydrogenocarbonate (100 mL) was added. The aqueous layer was extracted with dichloromethane (2 x 130 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was first purified on silica gel using ethyl acetate/dichloromethane (1/9) as an eluent to afford the title compound, methyl 3-[(tert-butoxy)carbonyl]amino}-2-[2-(4-methoxyphenyl)ethyl]amino}propanoate in 80% yield (2.4 g) as an yellow oil. 1H NMR (CDCl3): δ 1.49 (s, 9H), 2.8 (m, 3H), 2.94 (m, 1H), 3.3 (m, 1H), 3.44 (m, 1H), 3.52 (m, 1H), 3.78 (s, 3H), 3.85 (s, 3H), 5.04 (m, 1H), 6.89 (d, 2H), 7.18 (d, 2H); MS (ESI+): m/z = 353.2 [(M+H]+
80%	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;	99.d d) Methyl 3-{ r(tert-butoxy)carbonyllamino)-2-{ Γ2-(4- methoxyphenyPethyll amino jpropanoate (1-56) d) Methyl 3-{ r(tert-butoxy)carbonyllamino)-2-{ Γ2-(4- methoxyphenyPethyll amino jpropanoate (1-56) Sodium triacetoxyborohydride (2.21 g; 10.43 mmol; 1.1 eq) was added to a solution of 2-(4-methoxyphenyl)acetaldehyde (1-55) (1.28 g; 8.53 mmol; 0.9 eq) and methyl 2-amino-3-{ [(iert-butoxy)carbonyl] amino Jpropanoate (1-57) (2.07 g; 9.48 mmol; 1 eq) in dichloromethane (135 mL). The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium hydrogenocarbonate (100 mL) was added. The aqueous layer was extracted with dichloromethane (2 x 130 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was first purified on silica gel using ethyl acetate/dichloromethane (1/9) as an eluent to afford the title compound, methyl 3- { [(ieri-butoxy)carbonyl] amino } -2- { [2-(4-methoxyphenyl)ethyl] amino } propanoate in 80% yield (2.4 g) as an yellow oil. 1H NMR (CDC13): δ 1.49 (s, 9H), 2.8 (m, 3H), 2.94 (m, 1H), 3.3 (m, 1H), 3.44 (m, 1H), 3.52 (m, 1H), 3.78 (s, 3H), 3.85 (s, 3H), 5.04 (m, 1H), 6.89 (d, 2H), 7.18 (d, 2H); MS (ESI+): m/z = 353.2 [(M+H]+.

Reference： [1]Current Patent Assignee: VALNEVA SE - EP2664616, 2013, A1 Location in patent: Paragraph 0302-0303
[2]Current Patent Assignee: VALNEVA SE - WO2013/171281, 2013, A1 Location in patent: Page/Page column 150-151

40
[ 5703-26-4 ]
ethyl 2-amino-2-[(5-methoxypyridin-2-yl)carbamoyl]acetate hydrochloride [ No CAS ]
ethyl 2-[2-(4-methoxyphenyl)ethyl]amino}-2-[(5-methoxypyridin-2-yl)carbamoyl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium tris(acetoxy)borohydride In methanol; dichloromethane at 20℃; for 16h;	100.e e) Ethyl 2- { r2-(4-methoxyphenyl)ethyl1 amino I -2- r(5-methoxypyridin-2- vPcarbamoyll acetate (1-71) e) Ethyl 2- { r2-(4-methoxyphenyl)ethyl1 amino I -2- r(5-methoxypyridin-2- vPcarbamoyll acetate (1-71) Sodium triacetoxyborohydride (368 mg; 1.58 mmol; 1.1 eq) was added to a solution of 2-(4-methoxyphenyl)acetaldehyde (1-55) (237 mg; 1.58 mmol; 1 eq) and ethyl 2- amino-2-[(5-methoxypyridin-2-yl)carbamoyl]acetate hydrochloride (1-70) (457 mg; 1.58 mmol; 1 eq) in dichloromethane (21 mL). Methanol (1 mL) was added in order to obtain a homogeneous solution. The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium hydrogenocarbonate (20 mL) was added. The aqueous layer was extracted with dichloromethane (2 x 40 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel using ethyl acetate/dichloromethane (100/0 to 80/20) as an eluent to afford the title compound, ethyl 2-{ [2-(4-methoxyphenyl)ethyl]amino}-2-[(5-methoxypyridin-2-yl)carbamoyl] cetate in 59% yield (360 mg) as an yellow oil. 1H NMR (DMSO-d6): δ (ppm) 1.24 (t, 3H), 2.69 (m, 4H), 3.77 (s, 3H), 3.87 (s, 3H), 4.14 (q, 2H), 4.31 (m, 1H), 6.84 (d, 2H), 7.14 (d, 2H), 7.45 (d, 1H), 7.98 (d, 1H), 8.07 (s, 1H), 10.41 (s, 1H); MS (ESI+): m/z = 388.1 [M+H]+ .

Reference： [1]Current Patent Assignee: VALNEVA SE - WO2013/171281, 2013, A1 Location in patent: Page/Page column 167-168

41
[ 5703-26-4 ]
[ 347174-05-4 ]
ethyl 4-(cyclohexylamino)-3-((4-methoxybenzyl)amino)-benzoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 4551 - 4556

42
[ 5703-26-4 ]
(1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-octahydro-1H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol [ No CAS ]
(1S,3S,4R)-3-(hydroxymethyl)-4-((3aS,4R,5S,7aS)-4-((4-methoxyphenethylamino)methyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-4-methylcyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 25h;	41.B Synthesis of (1S,3S,4 R)-3-(hydroxymethyl)-4-((3aS,4R,5S,7aS)-4-((4-methoxyphenethylamino)methyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-4-methylcyclohexanol (Compound No. 81) B. To a mixture of Compound No. 80 (33 mg) and (1S,35,4R)-4-((3a5,4R, 5S, 7a5)-4-(ami nomethyl)-7a-methyl-1 -methyleneoctahyd ro- 1 H-i nden-5-yl )-3-(hydroxymethyl)-4-methylcyclohexanol (Compound No. 22, 59 mg, 0.18 mmol) in THF(1 .8 mL) was added sodium triacetoxyborohydride (78 mg, 0.37 mmol), and themixture was stirred at room temperature for 25 h. The mixture was diluted with 1:9MeOHCH2CI2 (15 mL) and washed with 1 N NaOH(aq) (10 mL). The aqueous layerwas extracted with CH2CI2 (2X1 0 mL), and the combined organic layers were dried(Mg504) and concentrated. The residue was purified by chromatography on silica gel(100:5:1 CH2CI2MeOHNH4OH) to give (1 S,35,4R)-3-(hydroxymethyl)-4-((3a5,4R,55,7a5)-4-((4-methoxyphenethylamino)methyl)-7a-methyl-1 -methyleneoctahydro-1 H-inden-5-yl)-4-methylcyclohexanol (Compound No. 81, 49 mg,58%) as a colourless foam. 1H NMR (CD3OD): 67.13 (d, J = 8.4 Hz, 2H), 6.86 (d, J =8.7 Hz, 2H), 4.61 (s, 2H), 3.77 (s, 3H), 3.58 (m, 1H), 3.40 (m, 1H), 2.98 (m, 1H), 2.61-2.75 (m, 6H), 2.44 (m, 1H), 2.09-2.24 (m, 2H), 1.12-1.80 (m, 15H), 0.76 (s, 3H), 0.70(s, 3H). ES-MS m/z456 ([M-f-1]).

Reference： [1]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2014/143561, 2014, A1 Location in patent: Page/Page column 130

43
[ 5703-26-4 ]
[ 26409-33-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With ammonium cerium (IV) nitrate; copper (II) trifluoroacetate hydrate; water In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;
72%	With ammonium acetate; sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 5h; Green chemistry;

Reference： [1]Li, Ziyuan; Huang, Xiaoqiang; Chen, Feng; Zhang, Chun; Wang, Xiaoyang; Jiao, Ning [Organic Letters, 2015, vol. 17, # 3, p. 584 - 587]
[2]Yan, Rulong; Zhou, Xiaoqiang; Li, Ming; Li, Xiaoni; Kang, Xing; Liu, Xingxing; Huo, Xing; Huang, Guosheng [RSC Advances, 2014, vol. 4, # 92, p. 50369 - 50372]

44
[ 101565-19-9 ]
[ 5703-26-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With oxalyl dichloride In ethanol; chloroform; water monomer at 20℃; for 1h;	General Procedure for Hydrolysis of Vinyl Ether 9 (Table 1): General procedure: To a solution of vinyl ether 9 (0.5mmol) in CHCl3 (4.5 mL),9 oxalyl chloride (63 mg, 0.5 mmol) in CHCl3 (0.5 mL)9 was added at rt. Tothis reaction mixture, ethanol (29 μL, 0.5 mmol) and H2O (9 μL, 0.5 mmol) were subsequently added andthe whole was stirred at rt. After reaction was completed (monitored by TLC), the reaction was quenchedby the addition of sat. aqueous solution of NaHCO3 and the mixture was subsequently extracted withCHCl3. The combined extracts were washed with brine, dried over Na2SO4, and condensed under reducedpressure. The residue was purified by column chromatography.
85%	With formic acid In dichloromethane for 16h; Reflux;	Enol ether hydrolysis reaction, general conditions General procedure: The purified enol ether product (E/Z mixture) from the first step was dissolved in dichloromethane (30 mL,entries 1-5) or dichloroethane (30 mL, entries 6-10), formic acid (98%, 3 mL) was added, and the mixture was refluxed for 3-36 h (see table 1). Reactions mixtures were monitored by TLC, when the reactions were deemed complete the mixtures were cooled to r.t, diluted with dichloromethane, and washed with aq NaHCO3. The organic layer was dried (MgSO4) and evaporated. In some cases (see Table 1) purification of the crude products on a short silica gel column (100:0 to 95:5 toluene-ethyl acetate gradient) wasperformed.
66%	With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;

59%	With hydrogenchloride; water monomer In tetrahydrofuran for 2h; Reflux;	4-Methoxyphenylacetaldehyde (5a) To a solution of 17a (2.46 g, 15 mmol) in THF (15 mL) wasadded 5% hydrochloric acid (7.5 mL), and the whole was refluxed for 2 h. After being cooled, water wasadded, and the mixture was extracted with Et2O. Combined organic layers were washed with saturatedsodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated. The residue waspurified by silica gel column chromatography (hexane/EtOAc = 4/1) to give 5a (1.35 g, 59%) as acolorless oil. 1H-NMR (300 MHz, CDCl3) δ: 3.62 (2H, d, J = 2.5 Hz), 3.81 (3H, s), 6.91 (2H, d, J = 8.8Hz), 7.13 (2H, d, J = 8.8 Hz), 9.72 (1H, t, J = 2.5 Hz)
	With formic acid In dichloromethane at 20℃;
	With toluene-4-sulfonic acid In water monomer; acetonitrile at 0 - 20℃; for 6h;
	With trifluoroacetic acid In dichloromethane; water monomer at 20℃; for 24h;	4.1.4. General procedure for synthesis of phenylacetaldehyde General procedure: To a stirred solution of 3a-e (2 mmol) in CH2Cl2 (200 mL) wasslowly added water (4 mL) and TFA (4 mL) successively at roomtemperature. After being stirred for 24 h, the mixture wasquenched with saturated NaHCO3 and extracted with CH2Cl2. TheCH2Cl2 solution was dried over MgSO4, filtered and concentrated.The residue was purified by chromatography eluted with petroleum ether/ethyl acetate (1: 20) to afford the product 4a-e in 49-75% yield (Scheme S1).
	With water monomer; tenofovir alafenamide In dichloromethane at 20℃; for 18h;

Reference： [1]Sakata, Ryo; Soeta, Takahiro; Ukaji, Yutaka [Heterocycles, 2015, vol. 91, # 3, p. 593 - 603]
[2]Al-Smadi, Derar; Enugala, Thilak Reddy; Norberg, Thomas; Kihlberg, Jan; Widersten, Mikael [Synlett, 2018, vol. 29, # 9, p. 1187 - 1190]
[3]Tian, Guilong; Fedoseev, Pavel; Van der Eycken, Erik V. [Chemistry - A European Journal, 2017, vol. 23, # 22, p. 5224 - 5227]
[4]Nishimura, Katsumi; Horii, Shinji; Tanahashi, Takao [Heterocycles, 2018, vol. 97, # 2, p. 865 - 876]
[5]Zaytsev, Andrey; Dodd, Barry; Magnani, Matteo; Ghiron, Chiara; Golding, Bernard T.; Griffin, Roger J.; Liu, Junfeng; Lu, Xiaohong; Micco, Iolanda; Newell, David R.; Padova, Alessandro; Robertson, Graeme; Lunec, John; Hardcastle, Ian R. [Chemical Biology and Drug Design, 2015, vol. 86, # 2, p. 180 - 189]
[6]Ezawa, Masatoshi; Togo, Hideo [European Journal of Organic Chemistry, 2017, vol. 2017, # 16, p. 2379 - 2384]
[7]Jiang, Long; Yin, Ruijuan; Wang, Xueting; Dai, Jiajia; Li, Jing; Jiang, Tao; Yu, Rilei [European Journal of Medicinal Chemistry, 2017, vol. 135, p. 24 - 33]
[8]Zhang, Kai; Guan, Xian; Zhang, Xiao; Liu, Lu; Yin, Ruijuan; Jiang, Tao [Marine Drugs, 2022, vol. 20, # 4]

45
[ 5703-26-4 ]
1-(2,4-dimethoxybenzyl)-5-methoxy-1,6-dihydropyrazin-2(3H)-one [ No CAS ]
[ 108-24-7 ]
1-(4-(2,4-dimethoxybenzyl)-6-methoxy-3-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-2-(4-methoxyphenyl)ethyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 1-(2,4-dimethoxybenzyl)-5-methoxy-1,6-dihydropyrazin-2(3H)-one With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #3: acetic anhydride With pyridine In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;	1-(4-(2,4-dimethoxybenzyl)-6-methoxy-3-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-2-(4-methoxyphenyl)ethyl acetate (12). To DMB-diketopiperazine 3 (338 mg, 1.21 mmol) dissolved in THF(5 mL) at -78 ° C was added LiHMDS solution (1.28 mL, 1M in THF) dropwise over 5 minutes.After allowing 15 minutes for enolization, a solution of aldehyde 2 (158.5 mg, 1.33 mmol in 2mL THF) was added slowly. After 30 minutes at -78°C, pyridine (152 μL, 1.57 mmol) andacetic anhydride (126 μL, 1.57 mmol) were added and the reaction mixture was allowed to warmto rt overnight (16 h). The reaction misture was concentrated in vacuo and re-dissolved indichloromethane (10 mL). This solution was washed with 0.1M HCl (10 mL) and the aqueouslayer was extracted with dichloromethane (3x10 mL). The combined organic layers were washedwith saturated NaHCO3 (40 mL), saturated NaCl (40 mL), dried (Na2SO4), filtered andconcentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel(10% to 60% EtOAc in hexanes with a constant 5% chloroform ternary solvent additive) toafford the acetoxy aldol adduct 12 (390 mg, 69% yield) as an inseparable mixture ofdiastereomers: TLC (60% EtOAc in hexanes) R = 0.76 (CAM/UV); IR (film) cm-1 3054, 2998,2948, 2837, 2358, 2336, 2060, 1741, 1701, 1652, 1615, 1587, 1558, 1515, 1489, 1465, 1457,1373, 1320, 1296, 1248, 1211, 1179, 1158, 1131, 1034, 938, 859, 833, 788, 735; 1H NMR (400MHz, CDCl3) 7.30-7.19 (m, 6H), 6.94-6.81 (m, 4H), 6.47-6.41 (m, 4H), 5.54-5.50 (m, 1H), 5.37-5.33 (m, 1H), 4.82-4.75 (m, J = 14.9 Hz, 4H), 4.42 (m, J = 14.4 Hz, 2H), 4.27 (m, J = 14.5 Hz,2H), 4.09 (d, J = 2.0 Hz, 1H), 3.89 (d, J = 2.0 Hz, 1H), 3.87-3.65 (m, 24H), 3.17-3.11 (m, 1H),3.04-2.91 (m, 3H), 1.87 (s, 3H), 1.70 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 170.1, 169.7,

Reference： [1]Leibowitz, Maren K.; Winter, Ethan S.; Scheerer, Jonathan R. [Tetrahedron Letters, 2015, vol. 56, # 44, p. 6069 - 6072]

46
[ 5703-26-4 ]
[ 4105-21-9 ]
1-(4-methoxyphenyl)-2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethane-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With [2,2]bipyridinyl; copper(I) bromide In toluene at 100℃; for 14h;	3 General procedure for dicarbonylation of imidazoheterocycles A mixture of imidazoheterocycles (0.52mmol), phenyl acetaldehyde (0.62mmol), CuBr (0.052mmol), 2,2-bipyridine (0.052mmol) in toluene (8mL) was heated at 100°C for 12-17h (TLC). Toluene was evaporated and the reaction mixture was directly subjected to silica gel column chromatography (Hexane/EtOAc, 9:1) to yield the dicarbonylated product 3, 5 as colored products in pure form.

Reference： [1]Shakoor, S. M. Abdul; Agarwal, Devesh S.; Kumar, Anil; Sakhuja, Rajeev [Tetrahedron, 2016, vol. 72, # 5, p. 645 - 652]

47
[ 5703-26-4 ]
[ 107-11-9 ]
[ 5958-02-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3732 - 3736

48
[ 5703-26-4 ]
[ 109-76-2 ]
[ 5958-02-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3732 - 3736

49
[ 5703-26-4 ]
[ 622-37-7 ]
[ 68809-41-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hydroxide at 20℃; for 0.666667h; Green chemistry; regioselective reaction;	Synthesis of triazoles; general procedure General procedure: The ionic liquid [bmim]PF6 (5.0 mL) was treated with KOH (40 mol%,22.4 mg), azides (1.0 mmol) and aldehydes (1.0 mmol). Then thereaction mixture was vigorously stirred at room temperature andmonitored by TLC. The products were filtrated from the reactionmixtures and recrystallised using pentane (PE)/ethyl acetate (EA)as the solvent. All the known compounds were characterised by their1H NMR and 13C NMR spectra.
90%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃; for 0.5h; regioselective reaction;
80%	In dimethyl sulfoxide at 20℃; for 1h;

Reference： [1]Jiang, Yuqin; Wu, Kai; Tan, Xuxia; Zhang, Dandan; Dong, Wenpei; Li, Wei; Xu, Guiqing; Zhang, Weiwei [Journal of Chemical Research, 2017, vol. 41, # 11, p. 631 - 635]
[2]Ramachary, Dhevalapally B.; Shashank, Adluri B.; Karthik [Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10420 - 10424][Angew. Chem., 2014, vol. 126, # 39, p. 10588 - 10592,5]
[3]Jiang, Yuqin; Li, Xingfeng; Zhao, Yaru; Jia, Shuhong; Li, Mingrui; Zhao, Zhiqi; Zhang, Ruili; Li, Wei; Zhang, Weiwei [RSC Advances, 2016, vol. 6, # 111, p. 110102 - 110107]

50
[ 5703-26-4 ]
4-methyl-N-(3-methylpent-3-en-1-yl)benzenesulfonamide [ No CAS ]
6-(4-methoxybenzyl)-4,5-dimethyl-1-tosyl-1,2,3,6-tetrahydropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With boron trifluoride diethyl etherate In dichloromethane at 40℃; for 21h; Inert atmosphere;	6-(4-Methoxybenzyl)-4,5-dimethyl-1-tosyl-1,2,3,6-tetrahydropyridine (9c) To a mixture of 4-methyl-N-(3-methylpent-3-en-1-yl)benzenesulfonamide(5b) (E/Z = 2.5:1) (254 mg, 1.00 mmol) and 4-methoxyphenylacetaldehyde(180 mg, 1.20 mmol) in abs CH2Cl2 (3 mL) was added BF3·OEt2 (49 μL, 57 mg, 0.40 mmol). The resulting mixture was stirredat 40 °C for 21 h. Column chromatography (pentane/EtOAc, 11:1) gave6-(4-methoxybenzyl)-4,5-dimethyl-1-tosyl-1,2,3,6-tetrahydropyridine(9c) (148 mg, 0.38 mmol, 38%) as a yellow oil.Rf = 0.41 (pentane/EtOAc, 10:1, phosphomolybdic acid).IR (ATR): 2930, 2360, 1739, 1512, 1335, 1244, 1155, 1091, 1035, 814,729, 661 cm-1.1H NMR (400 MHz, CDCl3): δ = 7.44-7.38 (m, 2 H, 14-H), 7.11 (d,3JH,H = 8.0 Hz, 2 H, 15-H), 7.07-7.02 (m, 2 H, 8-H), 6.80-6.74 (m, 2 H,9-H), 4.34-4.27 (m, 1 H, 5-H), 3.80 (s, 3 H, 19-H), 3.62-3.54 (m, 1 H, 1-Ha), 3.04 (ddd, 3JH,H = 14.5 Hz, 3JH,H = 11.7 Hz, 3JH,H = 5.1 Hz, 1 H, 1-Hb), 2.95 (dd, 2JH,H = 14.2 Hz, 3JH,H = 4.5 Hz, 1 H, 6-Ha), 2.72 (dd, 2JH,H = 14.3Hz, 3JH,H = 8.2 Hz, 1 H, 6H-b), 2.37 (s, 3 H, 17-H), 2.00-1.86 (m, 1 H, 2-Ha), 1.67 (s, 3 H, 12-H), 1.61-1.51 (m, 1 H, 2-Hb), 1.46 (s, 3 H, 11-H).13C NMR (101 MHz, CDCl3): δ = 158.3 (C10), 142.7 (C16), 138.1 (C13),130.6 (C8), 129.8 (C7), 129.2 (C15), 127.2 (C14), 126.2, 125.9 (C3, C4),113.8 (C9), 59.3 (C5), 55.3 (C19), 38.7 (C1), 38.2 (C6), 29.3 (C2), 21.6(C17), 19.0, 17.0 (C11, C12).HRMS (ESI): m/z [M + Na]+ calcd for C22H27NO3S + Na: 408.1604;found: 408.1615.

Reference： [1]Ploog, Jasper; Pongs, Juliane; Weber, Stefan; Maison, Wolfgang [Synthesis, 2017, vol. 49, # 3, p. 693 - 703]

51
[ 5703-26-4 ]
[ 2080-62-8 ]
8-methoxy-6-methyl-3-tosyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 40℃; for 21h; Inert atmosphere;	8-Methoxy-6-methyl-3-tosyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (6j) To a mixture of 4-methyl-N-(3-methylbut-3-en-1-yl)benzenesulfonamide (5a) (239 mg, 1.00 mmol) and (4-methoxyphenyl)acetaldehyde(180 mg, 1.20 mmol) in abs CH2Cl2 (3 mL) was added TMSOTf(36 μL, 44 mg, 0.20 mmol). The resulting mixture was stirred inCH2Cl2 at 40 °C for 21 h. Column chromatography (pentane/EtOAc,10:1) gave 8-methoxy-6-methyl-3-tosyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (6j) (199 mg, 0.54 mmol, 54%) as a yellowsolid.Mp 114-117 °C; Rf = 0.16 (pentane/EtOAc, 10:1, phosphomolybdicacid).IR (ATR): 2930, 2837, 2363, 1739, 1616, 1577, 1496, 1336, 1238, 1154,1093, 1044, 811, 682 cm-1.1H NMR (400 MHz, CDCl3): δ = 7.71 (d, 3JH,H = 8.3 Hz, 2 H, 16-H), 7.29(d, 3JH,H = 8.0 Hz, 2 H, 17-H), 6.84 (d, 3JH,H = 8.5 Hz, 1 H, 6-H), 6.79 (d,4JH,H = 2.7 Hz, 1 H, 3-H), 6.66 (dd, 3JH,H = 8.4 Hz, 4JH,H = 2.7 Hz, 1 H, 5-H),4.50-4.43 (m, 1 H, 9-H), 3.76 (s, 3 H, 20-H), 3.65 (dd, 2JH,H = 12.6 Hz,3JH,H = 3.9 Hz, 1 H, 11-Ha), 2.95 (dd, 2JH,H = 17.9 Hz, 3JH,H = 6.0 Hz, 1 H, 8-Ha), 2.71-2.55 (m, 2 H, 11-Hb, 8-Hb), 2.43 (s, 3 H, 19-H), 1.79-1.55 (m,3 H, 13-Ha, 13-Hb, 12-Ha), 1.43-1.29 (m, 4 H, 12-Hb, 14-H).13C NMR (101 MHz, CDCl3): δ = 158.3 (C4), 143.4 (C18), 143.1 (C2),138.1 (C15), 129.8 (C17), 128.9 (C6), 127.7 (C7), 127.2 (C16), 111.7(C5), 110.7 (C3), 55.4 (C20), 48.2 (C9), 40.1 (C12), 39.9 (C11), 38.8(C13), 33.6 (C8), 32.4 (C1), 28.0 (C14), 21.7 (C19).HRMS (ESI): m/z [M + H]+ calcd for C21H25NO3S + H: 372.1628; found:372.1642.

Reference： [1]Ploog, Jasper; Pongs, Juliane; Weber, Stefan; Maison, Wolfgang [Synthesis, 2017, vol. 49, # 3, p. 693 - 703]

52
[ 5703-26-4 ]
[ 762292-75-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 4-Methoxyphenylacetaldehyde With <i>L</i>-proline In N,N-dimethyl acetamide at 20℃; for 0.5h; Stage #2: With N-fluorobis(benzenesulfon)imide In N,N-dimethyl acetamide at 20℃; for 4h;	3 Example 3: Synthesis of 2,2-difluoro-2-(4-methoxyphenyl)ethanol 50 g of 2- (4-methoxyphenyl) acetaldehyde, 11 g of L-proline and 250 mL of dimethylacetamide are added to a 1000 mL reactor equipped with a stirrer, and the mixture is stirred at room temperature for 30 minutes. 209 g of N-fluorobenzenesulfonimide was added thereto, and the mixture was stirred at room temperature for 4 hoursDo not stir. After completion of the reaction, the layer is separated and dissolved in 250 mL of methanol. The temperature was lowered to 0 ° C, 56 g of sodium borohydride was added dropwise, the temperature was raised to room temperature and the mixture was stirred for 2 hours. After the reaction was completed, 2,2-difluoro-2- (4-methoxyphenyl) ethanol was obtained in a yield of 90%.

Reference： [1]Current Patent Assignee: SAMHWA PAINTS IND. CO.,LTD. - KR101706914, 2017, B1 Location in patent: Paragraph 0126; 0127

53
[ 5703-26-4 ]
[ 22171-15-9 ]
4-((3,4-bis(4-methoxyphenyl)-1H-pyrrol-1-yl)methyl)phenol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 24 - 33

54
[ 5703-26-4 ]
[ 22171-15-9 ]
1-(4-(benzyloxy)benzyl)-3,4-bis(4-methoxyphenyl)-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		General procedure: To a solution of the aldehyde 4a-e (1.0 mmol) in anhydrous THF(2.5 mL) was added the benzylamine 7a-j (1.0 mmol) under argonatmosphere. After stirred at room temperature for 0.5 h, AgOAc(334 mg, 2.0 mmol) and NaOAc (164 mg, 2.0 mmol) were addedsuccessively under argon, then the solution was heated at 60 C for8 h. The mixture was cooled down to room temperature, filteredthrough a pad of diatomite and the diatomite was washed withEtOAc. The filtrate was evaporated under reduced pressure and theresulting residue was purified by flash column chromatography togive the pure pyrroles. (The 1H and 13C NMR spectra data ofcompounds 8a-8r were submitted in the supplementary material).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 24 - 33

55
[ 5703-26-4 ]
[ 190018-05-4 ]
1-(3,4-bis(benzyloxy)benzyl)-3,4-bis(4-methoxyphenyl)-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 4-Methoxyphenylacetaldehyde; 3,4-dibenzyloxybenzyl amine In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: With silver(I) acetate; sodium acetate In tetrahydrofuran at 60℃; for 8h; Inert atmosphere;	4.1.7. General procedure for synthesis of pyrroles General procedure: To a solution of the aldehyde 4a-e (1.0 mmol) in anhydrous THF(2.5 mL) was added the benzylamine 7a-j (1.0 mmol) under argonatmosphere. After stirred at room temperature for 0.5 h, AgOAc(334 mg, 2.0 mmol) and NaOAc (164 mg, 2.0 mmol) were addedsuccessively under argon, then the solution was heated at 60 °C for8 h. The mixture was cooled down to room temperature, filteredthrough a pad of diatomite and the diatomite was washed withEtOAc. The filtrate was evaporated under reduced pressure and theresulting residue was purified by flash column chromatography togive the pure pyrroles. (The 1H and 13C NMR spectra data ofcompounds 8a-8r were submitted in the supplementary material).

Reference： [1]Jiang, Long; Yin, Ruijuan; Wang, Xueting; Dai, Jiajia; Li, Jing; Jiang, Tao; Yu, Rilei [European Journal of Medicinal Chemistry, 2017, vol. 135, p. 24 - 33]

56
[ 5703-26-4 ]
[ 62-53-3 ]
[ 1609013-26-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) nitrate trihydrate; oxygen In N,N-dimethyl-formamide at 100℃; for 12h;	Typical Procedure General procedure: To a reaction tube charged with copper nitrate trihydrate (12.1 mg, 0.05mmol, 20 mol%) and TEMPO (78.1 mg, 0.5 mmol, 2 equiv) under O2 (1 atm) was added asolution of aniline 2 (0.25 mmol, 1 equiv), acetaldehyde 3 (1 mmol, 4 equiv) and H2O (135 μL,7.5 mmol, 30 equiv) in DMF (3 mL). The reaction mixture was then stirred at 100 °C for 12 hours.After cooling to room temperature, the mixture was diluted with ethyl acetate, washed withsaturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate, andconcentrated in vacuo to give dark residue, which was purified by flash chromatography (usingpetroleum ether and ethyl acetate as the effluent) on silica gel to afford the 2-aroylquinolineproducts 9a - 9r

Reference： [1]Li, Ziyuan; Wang, Xiaoyang; Ma, Lifang; Jiao, Ning [Synlett, 2017, vol. 28, # 13, p. 1581 - 1585]

57
1-(4-fluorobenzyl)-N-(pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
[ 5703-26-4 ]
1-(4-fluorobenzyl)-N-(1-(4-methoxyphenethyl)pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1-(4-fluorobenzyl)-N-(pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-amine; 4-Methoxyphenylacetaldehyde With acetic acid; N-ethyl-N,N-diisopropylamine In ethanol at 40℃; for 1h; Stage #2: With sodium cyanoborohydride In ethanol at 40℃; for 18h;	8 4.1.8 1-(4-Fluorobenzyl)-N-(1-(4-methoxyphenethyl)pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-amine To a solution of 135 1-(4-fluorobenzyl)-N-(pyrrolidin-3-yl)-1H-benzo[d]imidazol-2-amine (78mg, 0.25mmol) and 141 2-(4-methoxyphenyl)acetaldehyde (50mg, 0.30mmol) in 144 EtOH (5mL), was added 145 diisopropylethylamine (83µL, 0.50mmol) and 146 acetic acid (14µL, 0.75mmol). The mixture was stirred at 40°C for 1 h. Then, 147 sodium cyanoborohydride (19mg, 0.30mmol) was added and the mixture was stirred at 40°C overnight. The solvents were removed under reduced pressure and the residue was diluted with a saturated NaHCO3 solution, extracted with EtOAc and dried over Na2SO4. The solvent was removed under reduced pressure. The crude residue was purified by silica gel flash column chromatography to give the 148 title compound as slight yellow solid (96mg, 86%). 1H NMR (300MHz, MeOD) δ=7.38 (d, J=7.8Hz, 1H), 7.16-6.96 (m, 9H), 6.86-6.78 (m, 2H), 5.33 (s, 2H), 3.72 (s, 3H), 3.70-3.59 (m, 2H), 3.58-3.50 (m, 1H), 3.48-3.34 (m, 2H), 2.87-2.66 (m, 4H), 2.24-2.10 (m, 1H), 1.88-1.74 (m, 1H)ppm. 13C NMR (75MHz, MeOD) δ=163.54 (d, J=244.7Hz), 159.76, 157.35, 142.56, 136.96, 134.47 (d, J=3.2Hz), 132.44, 130.59, 128.89 (d, J=8.2Hz), 123.13, 121.66, 116.64 (d, J=21.4Hz), 115.02, 109.79, 58.43, 56.10, 55.65, 50.57, 49.83, 47.83, 35.59, 31.89ppm. HRMS m/z [M+H]+ calcd for C27H30FN4O: 445.2398, found: 445.2403.

Reference： [1]Tian, Junjun; Vandermosten, Leen; Peigneur, Steve; Moreels, Lien; Rozenski, Jef; Tytgat, Jan; Herdewijn, Piet; Van den Steen, Philippe E.; De Jonghe, Steven [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6332 - 6344]

58
[ 5703-26-4 ]
[ 622-79-7 ]
[ 116557-81-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hydroxide at 20℃; for 1.16667h; Green chemistry; regioselective reaction;	Synthesis of triazoles; general procedure General procedure: The ionic liquid [bmim]PF6 (5.0 mL) was treated with KOH (40 mol%,22.4 mg), azides (1.0 mmol) and aldehydes (1.0 mmol). Then thereaction mixture was vigorously stirred at room temperature andmonitored by TLC. The products were filtrated from the reactionmixtures and recrystallised using pentane (PE)/ethyl acetate (EA)as the solvent. All the known compounds were characterised by their1H NMR and 13C NMR spectra.

Reference： [1]Jiang, Yuqin; Wu, Kai; Tan, Xuxia; Zhang, Dandan; Dong, Wenpei; Li, Wei; Xu, Guiqing; Zhang, Weiwei [Journal of Chemical Research, 2017, vol. 41, # 11, p. 631 - 635]

59
[ 5703-26-4 ]
[ 14630-40-1 ]
1-(4-methoxyphenyl)-4-(trimethylsilyl)-3-butyn-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: Bis(trimethylsilyl)ethyne With methyllithium; lithium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran; diethyl ether at -78 - 20℃; for 7h; Inert atmosphere;	1-(4-Methoxyphenyl)-4-(trimethylsilyl)-3-butyn-2-ol (15) Using a modification of Zweifel’s 12 procedure, (trimethylsilyl)ethynyllithiumwas generated by injecting MeLi-LiBr in Et2O (1.5 M; 2.83 mL,4.25 mmol) into a stirred solution of 8 (915 μL, 724 mg, 4.25 mmol) inTHF (5 mL) at 0 °C. The mixture was stirred for 30 min at 0 °C, then 30 min at r.t., then cooled to -78 °C, whereupon a solution of 14 (532mg, 3.54 mmol) in THF (5 mL) was added slowly by syringe. Warming to r.t. over 7 h was followed by quenching with H2O (0.5 mL). After stirring for 10 min, the volatiles were removed by rotary evaporation, and the residue was partitioned between Et2O (20 mL) and aq HCl (2N; 40 mL). The layers were separated, and the aqueous phase was extracted with Et2O (3 × 20 mL). The combined organic phases were washed with sat. aq NaHCO3 (40 mL) and dried over Na2SO4. The solvent was removed by rotary evaporation and the remaining light yellow oil distilled to provide 15 (701.4 mg, 80%) as a clear viscous liquid; bp (Kugelrohr, 0.2 torr) 230 °C. IR (film): 3450 (br), 2955, 2925, 2834, 2172, 1613, 1514, 1301, 1243,1040, 844, 759 cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.18 (d, J = 8.6 Hz, 2 H), 6.83 (d, J = 8.7Hz, 2 H), 4.48 (dd, J = 12.0, 6.1 Hz, 1 H), 3.77 (s, 3 H), 2.92 (ABXm, 2 H),2.21 (d, J = 5.6 Hz, 1 H), 0.16 (s, 9 H).13C NMR (75 MHz, CDCl3): δ = 158.3, 130.7, 128.4, 113.5, 106.2, 90.0,63.5, 55.0, 42.9, -0.29.MS (EI, 70 eV): m/z (%) = 248 ([M+], 15), 233 (11), 230 (5), 215 (7), 122(67), 121 (100), 83 (46), 75 (63), 73 (22).UV/VIS (MeCN): λmax (log ε) = 226 (4.04), 267 (sh, 3.10), 276 (3.26),283 nm (3.19).Anal. Calcd for C14H20O2Si: C, 67.69; H, 8.12. Found: C, 67.78; H, 8.09.

Reference： [1]Aechtner, Tobias; Barry, David A.; David, Ellen; Ghellamallah, Cédric; Harvey, Daniel F.; De La Houpliere, Alix; Knopp, Monika; Malaska, Michael J.; Pérez, Dolores; Schärer, Kaspar A.; Siesel, Brian A.; Vollhardt, K. Peter C.; Zitterbart, Robert [Synthesis, 2018, vol. 50, # 5, p. 1053 - 1089]

60
[ 603-76-9 ]
[ 5703-26-4 ]
1-(4-methoxyphenyl)-2-(1-methyl-1H-indol-3-yl)ethane-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; oxygen; copper(I) bromide In 1,4-dioxane at 90℃; for 8h; Green chemistry;	6 Synthesis of Compound 6ab: 1 mmol (0.15 g) of 4-methoxyphenylacetaldehyde 6a,1.5 mmol (0.2 g) of 1-methylindole 6b,0.05mmol(0.007g) cuprous bromide,0.2 mmol (0.016 g) of pyridine was added to the reaction tube,Then, after adding the reaction solvent 1,4-dioxane (3 mL), in an oxygen atmosphere,Stir at a temperature of 90 ° C for 8 hours.After the end of the reaction by thin layer chromatography,The product 6ab (0.25 g) yield was obtained by direct column chromatography: 87%;

Reference： [1]Current Patent Assignee: NANJING TECH UNIVERSITY - CN108863895, 2018, A Location in patent: Paragraph 0047-0050

61
[ 5703-26-4 ]
[ 824-79-3 ]
[ 171743-15-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 4-Methoxyphenylacetaldehyde With acetic anhydride In neat (no solvent) at 25℃; for 0.166667h; Stage #2: sodium 4-methylbenzenesulfinate In neat (no solvent) at 25℃; for 4h; stereoselective reaction;	β-Sulfonyl Styrenes 1a-ac; General Procedure General procedure: Ac2O (510 mg, 5.0 mmol) was added to a stirred solution of the respectivearylacetaldehyde 2 (5.0 mmol) at 25 °C. The reaction mixturewas stirred at 25 °C for 2 min. PPA (490 mg, 5.0 mmol) was addedslowly to the reaction mixture at 25 °C over 3 min. The mixture wasstirred at 25 °C for 5 min. Then, the corresponding sodium sulfinateRSO2Na 3 (10.0 mmol) was added to the mixture at 25 °C and themixture was stirred at 25 °C for 4 h. The residue was diluted with H2O(20 mL) and the mixture was extracted with CH2Cl2 (3 × 20 mL). Thecombined organic layers were washed with aq NaHCO3 (3 × 10 mL),brine, dried, filtered and evaporated to afford the crude product underreduced pressure. Purification on silica gel (hexanes/EtOAc 8:1 to4:1) afforded compounds 1a-ac (Table 2).

Reference： [1]Chang, Meng-Yang; Wu, Yan-Shin; Hsiao, Yu-Ting [Synthesis, 2018, vol. 50, # 23, p. 4651 - 4658]

62
[ 5703-26-4 ]
(R)-1-(4-benzyloxy-3-methoxyphenethyl)-3-[1-(1-naphthyl)ethyl]urea [ No CAS ]
(1R)-7-benzyloxy-6-methoxy-1-(4-methoxybenzyl)-2-[N-((R)-1-(1-naphthyl)ethyl)carbamoyl]-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
(1S)-7-benzyloxy-6-methoxy-1-(4-methoxybenzyl)-2-[N-((R)-1-(1-naphthyl)ethyl)carbamoyl]-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 65% 2: 34%	With trifluoroacetic acid In dichloromethane at -20℃; for 16h;	(1R)- and (1S)-7-Benzyloxy-6-methoxy-1-(4-methoxybenzyl)-2-[N-((R)-1-(1-naphthyl)ethyl)carbamoyl]-1,2,3,4-tetrahydroisoquinoline ((1R)- and (1S)-18a). General Procedure for the Pictet-Spengler Reaction To a solution of urea 7a (227 mg, 0.5 mmol) and aldehyde 5a (83 mg, 0.55 mmol) in CH2Cl2(2.5 mL) was added trifluoroacetic acid (0.26 mL, 3.5 mmol) at -20 °C. After 16 h at the sametemperature, water was added, and the whole was extracted with EtOAc. Combined organic layers werewashed with saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated.The residue was purified by silica gel column chromatography (hexane/EtOAc = 1:1) to give (1R)-18a(190 g, 65%) and (1S)-18a (99 mg, 34%), respectively. (1R)-18a: white foam of mp 98-100 °C. [α]24D-70.2 (c 1.00, benzene). IR (Nujol) cm-1: 3343, 1612, 1511. 1H-NMR (300 MHz, CDCl3) δ: 1.32 (3H, d, J= 6.6 Hz), 2.52 (1H, ddd, J = 15.9, 5.2, 4.5 Hz), 2.74-2.85 (2H, m), 2.84 (1H, dd, J = 13.3, 5.0 Hz), 2.96(1H, dd, J = 13.3, 7.5 Hz), 3.18 (1H, ddd, J = 12.6, 9.4, 4.5 Hz), 3.81 (3H, s), 3.85 (3H, s), 4.01 (1H, d, J= 7.4 Hz), 4.77 (1H, dd, J = 7.5, 5.0 Hz), 5.00 (2H, s), 5.63 (1H, m), 6.45 (1H, s), 6.59 (1H, s), 6.84 (2H,d, J = 8.5 Hz), 7.00 (2H, d, J = 8.5 Hz), 7.27-7.51 (9H, m), 7.75 (1H, d, J = 8.2 Hz), 7.83 (1H, dd, J = 7.1,2.2 Hz), 8.05 (1H, dd, J = 7.4, 2.3 Hz). 13C-NMR (75 MHz, CDCl3) δ: 21.7, 28.2, 42.2, 43.4, 45.9, 55.6,56.2, 57.9, 71.7, 111.9, 113.8, 114.3, 122.4, 123.8, 125.4, 125.8, 126.5, 127.5, 127.8, 128.0, 128.1, 128.6,128.7, 128.8, 130.8, 131.0, 131.2, 134.1, 137.3, 139.9, 146.4, 148.7, 157.0, 158.8. MS (EI) m/z: 388, 341,268, 250, 198, 182. Anal. Calcd for C38H38N2O40.25H2O: C, 77.20; H, 6.56; N, 4.74. Found: C, 77.27; H,6.59; N, 4.79. (1S)-18a: white foams of mp 105-108 °C. [α]23D +54.4 (c 1.00, benzene). IR (Nujol) cm-1:3343, 1612, 1511. 1H-NMR (300 MHz, CDCl3) δ: 1.53 (3H, d, J = 6.9 Hz), 2.57 (1H, ddd, J = 15.9, 5.2,4.7 Hz,), 2.76-2.82 (2H, m), 2.82 (1H, dd, J = 13.3, 6.0 Hz), 2.96 (1H, dd, J = 13.3, 7.0 Hz), 3.23 (1H,ddd, J = 12.9, 9.6, 4.7 Hz), 3.64 (3H, s), 3.86 (3H, s), 4.35 (1H, d, J = 6.6 Hz), 4.91 (1H, dd, J = 7.0, 6.0Hz), 4.98 (2H, s), 5.66 (1H, m), 6.41 (1H, s), 6.60 (2H, d, J = 8.8 Hz), 6.61 (1H, s), 6.87 (2H, d, J = 8.8Hz), 7.16 (1H, d, J = 7.1 Hz), 7.36-7.54 (8H, m), 7.75 (1H, d, J = 8.2 Hz), 7.84 (1H, dd, J = 7.1, 2.2 Hz),8.07 (1H, dd, J = 7.4, 2.5 Hz). 13C-NMR (75 MHz, CDCl3) δ: 22.5, 28.1, 42.3, 46.6, 45.9, 55.3, 56.3, 57.9,71.5, 111.9, 113.8, 114.3, 122.4, 123.8, 125.4, 125.8, 126.4, 127.5, 127.7, 128.0, 128.1, 128.2, 128.7,128.9, 130.6, 130.7, 131.2, 134.1, 137.3, 139.9, 146.4, 148.7, 157.0, 158.8. MS (EI) m/z: 388, 268, 198,182. Anal. Calcd for C38H38N2O4: C, 77.79; H, 6.53; N, 4.77. Found: C, 77.52; H, 6.62; N, 4.77

Reference： [1]Nishimura, Katsumi; Horii, Shinji; Tanahashi, Takao [Heterocycles, 2018, vol. 97, # 2, p. 865 - 876]

63
1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(4-methoxyphenoxy)-1,3-propanediol [ No CAS ]
[ 5703-26-4 ]
[ 123-11-5 ]
[ 134-96-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 61% 2: 38% 3: 6%	With oxygen; vanadium(V) oxytriisopropoxide In acetonitrile at 25 - 40℃; for 12h; Irradiation; Sealed tube;

Reference： [1]Liu, Huifang; Li, Hongji; Luo, Nengchao; Wang, Feng [ACS Catalysis, 2020, vol. 10, # 1, p. 632 - 643]

64
[ 672-13-9 ]
[ 5703-26-4 ]
[ 149-73-5 ]
2,4-dimethoxy-3-(4-methoxyphenyl)-6-nitrochromane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With trifluorormethanesulfonic acid In toluene at 60℃; for 24h; Inert atmosphere; stereoselective reaction;	General Procedure for the Synthesis of 3-Substituted Chromanes General procedure: Salicylaldehyde 1 (0.50 mmol), aliphatic aldehyde 2 (1.50 mmol) and trimethyl orthoformate (2.00mmol) were dissolved in dry toluene (5.0 mL) under nitrogen. Trifluoromethanesulfonic acid (20mol%) was added into the reaction mixture. After being stirred at 60 °C for 24 h, the reactionmixture was quenched with 5% aq. NaHCO3. The organic layer was separated and the aqueous layerwas extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and filtered.The filtrate was concentrated in vacuo. The resulting residue was purified by columnchromatography on silica gel (hexane/ethyl acetate = 30/1) to afford 3-substituted chromane 3 or 4.

Reference： [1]Asada, Yosuke; Honda, Kiyoshi; Hoshino, Yujiro; Kishimoto, Mami; Ohtsuka, Naoya; Sunaga, Shuto; Tanaka, Kenta; Tanaka, Yuta; Ueno, Ko [Synlett, 2020, vol. 31, # 12, p. 1197 - 1200]

65
[ 5703-26-4 ]
2-(4-methoxyphenyl)ethan-1-d-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With samarium diiodide; water-d2 In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; regioselective reaction;	31 Example 31 Intoa 25mL single-necked round bottom flask under the protection of argon, add samarium diiodide (SmI2) in tetrahydrofuran (0.100mol/L) 7.50mL, compound 1ae 45.1mg (0.300mmol), heavy water 120mg (6.00mmol) ).The reaction mixture was stirred at room temperature for 15 min, after which air was passed through to quench the reaction.Ethyl acetate and 1M hydrochloric acid solution were added for extraction, the organic phase was dried, concentrated, and column chromatography was separated to obtain 32.2 mg of the target compound 2ae, with a yield of 70% and a deuteration rate of 98%.
70%	With samarium diiodide; water-d2 In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; chemoselective reaction;	3.4 General Procedure for the Reductive Deuteration of Aldehydes by SmI2-D2O General procedure: To a solution of samarium (II) iodide (0.100 M in THF; 7.50 mL, 0.750 mmol, 2.50 equiv),was added deuterium oxide (120 mg, 6.00 mmol, 20.0 equiv). A characteristic burgundy redcolor of SmI2-D2O complex was observed. A solution of aldehydes (0.300 mmol, 1.00 equiv)in THF (1.0 mL) was then added under Ar at room temperature and stirred vigorously. After 15min, excess SmI2 was oxidized by bubbling air through the reaction mixture. The reactionmixture was diluted with EtOAc (10 mL) and HCl (5.0 mL, 1.0 M, aq). The aqueous layer wasextracted with EtOAc (3 × 10 mL), organic layers were combined, washed with Na2S2O3 (2 ×5.0 mL, sat., aq), dried over Na2SO4, filtered and concentrated. The crude product was purifiedby flash chromatography (silica, 10-25% EtOAc/Hexane). The sample was analyzed by 1HNMR (CDCl3, 300 MHz) to obtain the deuterium incorporation.

Reference： [1]Current Patent Assignee: CHINA AGRICULTURAL UNIVERSITY - CN112939732, 2021, A Location in patent: Paragraph 0037; 0169-0172
[2]Li, Hengzhao; Hou, Yuxia; Lai, Zemin; Ning, Lei; Li, Ailing; Li, Yixuan; An, Jie [Synlett, 2021, vol. 32, # 12, p. 1241 - 1245]

66
[ 5703-26-4 ]
[ 1576-35-8 ]
[ 2943-42-2 ]
3-(4-methoxybenzyl)-4-(4-methoxyphenyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 73%	With dodecatungstosilic acid In 1,4-dioxane at 100℃; for 3h; Green chemistry; regioselective reaction;	Procedures for Synthesis of 4 and 5 General procedure: In a reaction vial of 4 mL, epoxides or aldehydes (0.4 mmol), sulfonyl hydrazides (0.4 mmol), H4SiW12O40 (4 mol%) and 1,4-dixone (1 mL) were added. Then the reaction was carried out in screw cap vial with a Teflon seal at 100 °C for 3 h. After cooling to room temperature, the mixture was further purified by column chromatography (petroleum ether/EtOAc) to afford the desired products.

Reference： [1]Yang, Guoping; Xie, Xuanjie; Cheng, Mengyuan; Gao, Xiaofei; Lin, Xiaoling; Li, Ke; Cheng, Yuanyuan; Liu, Yufeng [Chinese Chemical Letters, 2022, vol. 33, # 3, p. 1483 - 1487]

67
[ 5703-26-4 ]
[ 17356-08-0 ]
[ 2104-04-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine In dimethyl sulfoxide at 80℃; for 0.025h; Green chemistry;	General procedure for the catalytic synthesis of 2-aminothiazoles General procedure: A mixture of methylcarbonyl (1 mmol), thiourea (1.5 mmol), I2(1 mmol) and Nizeolite-Im-IL (15 mg) in DMSO (2 mL) was stirred at 80 °C for desired time. Afterthe satisfactory completion of the reaction (monitored by TLC), the nanocatalystwas separated through centrifugation. The reaction media (DMSO) was quenchedby adding ammonia to pH = 9-10 to give the solid products. Finally, the pure productwas recrystallized from ethanol at a high yield. All 2-aminothiazole products areknown and were identified by comparing their melting point, FT-IR and 1H NMRwith authentic samples.

Reference： [1]Kalhor, Mehdi; Zarnegar, Zohre [Research on Chemical Intermediates, 2022, vol. 48, # 2, p. 519 - 540]

68
[ 5703-26-4 ]
tert-butyl 2-(2-(2-isopropylphenyl)-6-oxopiperazin-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]
tert-butyl 2-(2-(2-isopropylphenyl)-4-(4-methoxyphenethyl)-6-oxopiperazin-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 4-Methoxyphenylacetaldehyde; tert-butyl 2-(2-(2-isopropylphenyl)-6-oxopiperazin-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate With acetic acid In 1,2-dichloro-ethane at 25℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 25℃; for 12h;	1 Step 1: tert-butyl 2- (2- (2-isopropylphenyl) -4- (4-methoxyphenethyl) -6-oxopiperazin-1-yl) -7-azaspiro [3.5] nonane-7-carboxylate To a solution of tert-butyl 2- (2- (2-isopropylphenyl) -6-oxopiperazin-1-yl) -7-azaspiro [3.5] nonane-7-carboxylate (1.0 g, 2.26 mmol) in DCE (20 mL) was added 2- (4- methoxyphenyl) acetaldehyde (510 g, 3.40 mmol) and HOAc (0.27 g, 4.52 mmol) . After stirred at 25 for 1 hr, then NaBH (OAc)3(0.96 g, 4.52 mmol) was added. The mixture was stirred at 25 for 12 hrs. Then aqueous NH4Cl (20 mL) was added to the mixture and extracted with DCM (20 mL × 3) . The combined organic phases were washed with brine (20 mL × 2) , dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (silica gel, eluent: PE/EA (v/v) = 1/1) to give tert-butyl 2- (2- (2-isopropylphenyl) -4- (4-methoxyphenethyl) -6-oxopiperazin-1-yl) -7-azaspiro [3.5] nonane-7-carboxylate (0.85 g, yield: 65%) as a yellow solid.1H NMR (400 MHz, CDCl3) δ ppm: 7.36-7.29 (m, 2H) , 7.19-7.13 (m, 1H) , 7.08-7.05 (m, 1H) , 6.90 (br d, J= 8.4 Hz, 2H) , 6.73 (d, J= 8.4 Hz, 2H) , 5.05 (m, 1H) , 4.23 (br s, 1H) , 3.77 (s, 3H) , 3.39 (m, 1H) , 3.27-3.15 (m, 6H) , 2.88 (m, 1H) , 2.67 (m, 1H) , 2.61-2.48 (m, 4H) , 2.22 (m, 1H) , 1.97 (br s, 1H) , 1.82 (br s, 1H) , 1.61 (br s, 1H) , 1.42 (s, 10H) , 1.33-1.38 (m, 2H) , 1.29 (m, 6H) .

Reference： [1]Current Patent Assignee: BEIGENE LTD. - WO2021/208963, 2021, A1 Location in patent: Paragraph 0342-0344

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	5703-26-4	MDL No. :	MFCD02261769
Formula :	C₉H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NRIVMXXOUOBRAG-UHFFFAOYSA-N
M.W :	150.17	Pubchem ID :	79782
Synonyms :

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.91
TPSA :	26.3 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Log Po/w (iLOGP) :	1.64
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	2.31
Consensus Log Po/w :	1.64

[ CAS No. 5703-26-4 ]

Quality Control of [ 5703-26-4 ]

Related Doc. of [ 5703-26-4 ]

Product Details of [ 5703-26-4 ]

Calculated chemistry of [ 5703-26-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5703-26-4 ]

Application In Synthesis of [ 5703-26-4 ]

[ 5703-26-4 ] Synthesis Path-Upstream 1~4

[ 5703-26-4 ] Synthesis Path-Downstream 1~68

Related Functional Groups of
[ 5703-26-4 ]

Aryls

Aldehydes

Ethers

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) :	-1.85
Solubility :	2.14 mg/ml ; 0.0143 mol/l
Class :	Very soluble
Log S (Ali) :	-1.54
Solubility :	4.38 mg/ml ; 0.0291 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.86
Solubility :	0.208 mg/ml ; 0.00138 mol/l
Class :	Soluble

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

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

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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
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P401
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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. 5703-26-4 ]

Quality Control of [ 5703-26-4 ]

Related Doc. of [ 5703-26-4 ]

Product Details of [ 5703-26-4 ]

Calculated chemistry of [ 5703-26-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5703-26-4 ]

Application In Synthesis of [ 5703-26-4 ]

[ 5703-26-4 ] Synthesis Path-Upstream 1~4

[ 5703-26-4 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 5703-26-4 ]

Aryls

Aldehydes

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5703-26-4 ]