Name: 103863-15-6|3-Phenylpicolinic acid|96%
Brand: Ambeed
SKU: A368724
Price: 75.0 USD
Availability: InStock
Rating: 95 (27 reviews)

1
[ 3256-89-1 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
84.5%	With potassium permanganate for 6h; Heating;
	With potassium permanganate; water

Reference： [1]Pillai; Nand [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 892 - 894]
[2]Ishiguro et al. [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 220,223][Chem.Abstr., 1958, p. 11846]

2
[ 103863-15-6 ]
[ 130943-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In acetic acid for 24h;
	With hydrogen In methanol for 36h;	E To a suspension of platinum oxide hydrate (1 g) in methanol (10 ml) was added a solution of 3- phenylpyridine-2-carboxylic acid (10.5 g, 52.8 mmol) in methanol (20 ml). The reaction was charged with 1 atm hydrogen gas and allowed to stir for 36 h. The reaction suspension was filtered and concentrated in vacuo to yield a solid residue which was dissolved in water (20 ml). To the solution were added acetone (20 ml) and sodium bicarbonate (13.3 g, 158 mmol), followed by di-/er/-butyldicarbonate (12.7 g, 58 mmol) with vigorous stirring. The resulting reaction suspension was allowed to stir for 12 h, at which point the pH was adjusted to 5.5 using IM phosphoric acid. The product was extracted with EtOAc (2 x 50 ml), and the organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to yield -(tert- butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid as an oily residue which crystallized on standing (8.2 g). LCMS (M+H) = 306.1.
	With Adam’s catalyst; hydrogen In methanol at 20℃;	1 Step 1: 3-Phenylpiperidine-2-carboxylic acid A solution of 3-phenyl picolinic acid (1 .9949 g,10.01 mmol) in methanol (16 mE) was added to a suspension of platinum (IV) oxide hydrate (0.1956 g, 0.798 mmol) in methanol (4 mE), and the mixture was degassed and charged with hydrogen gas from a balloon. The reaction mixture was stirred for 2.25 hours at room temperature. A sample of the reaction mixture was checked by ECMS and compared to a sample of starting material. Strong peaks for the starting material and the desired product were observed along with a weak over-reduced by-product. The hydrogen balloon was removed and the reaction was flushed with nitrogen, sealed, and left overnight. In the morning, a fresh hydrogen balloon was attached and the reaction was charged and stirred for 4.5 hours at room temperature. The balloon was removed, and the reaction mixture was diluted with dichloromethane and filtered through celite resulting in removal of a black solid. The filtrate was concentrated and left under vacuum for 30 minutes to yield 3-phenylpiperidine-2-carboxylic acid (2.0188 g, 98%) as a dark brown solid. MS (ESI) mlz 206.11 (M+H). The crude product was used in subsequent steps without further purification.

Reference： [1]Pillai; Nand [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 892 - 894]
[2]Current Patent Assignee: MERCK & CO INC - WO2008/36316, 2008, A2 Location in patent: Page/Page column 33-34
[3]Current Patent Assignee: MERCK & CO INC - US2016/229839, 2016, A1 Location in patent: Paragraph 0299

3
[ 103863-15-6 ]
[ 57955-12-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With methanesulfonic acid at 80℃; for 1h;	5 <Synthesis of Intermediate 116-14> Intermediate 116-13 28.58g (143.46mmol) was dissolved in 130ml of MsOH, heated to 80 and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, washed with saturated NaHCO3 aqueous solution, and filtered. The solid was dried, followed by column, and recrystallized with MC/PE to obtain 20.80 g of intermediate 116-14 in a yield of 80%.
40%	With polyphosphoric acid for 5h;	2.2.1. Synthesis of azafluorenone (4a-d) General procedure: (a) Halopicolinic acid (2.69 g, 13.31 mmol), phenylboronic acid(2.44 g, 19.97 mmol), 2M aqueous potassium carbonate (20 mL), palladiumacetate (0.14 g, 0.62 mmol), triphenylphosphine (0.70 g,2.67 mmol), and 1,4-dioxane (50 mL) were mixed and refluxed undernitrogen for 24 h. The reaction mixture was cooled to room temperatureand added aqueous sodium hydroxide (NaOH) (1 M, 35 mL) and dichloromethane(CH2Cl2) (20 mL). The aqueous layer was acidified topH=2-3 by using citric acid (1 M) followed by extraction with Etheracetate (EtOAc). The combined organic layers were dried over magnesiumsulfate (MgSO4), filtered, and concentrated to give off the crudeproduct. A mixture of the crude product and 50 g polyphosphoric acidwas heated at 210 °C for 5 h and then stop the reaction. After themixture had cooled to 140 °C, some ice and water were added slowly todilute the mixture. Then aqueous sodium hydroxide was added to makethe pH≥7, and the aqueous layer was extracted with EtOAc. Thecombined extracts were dried with MgSO4 and concentrated to provide0.96 g. The residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate 6:1) to give the desired product.
4.2 g	With PPA Heating;

Reference： [1]Current Patent Assignee: NANJING TOPTO SEMICONDUCTOR MATERIAL CO LTD - KR2020/108163, 2020, A Location in patent: Paragraph 0386; 0397-0400
[2]Wu, Peng; Zhu, Jun; Zhang, Zhen; Dou, Dehai; Wang, Hedan; Wei, Bin; Wang, Zixing [Dyes and Pigments, 2018, vol. 156, p. 185 - 191]
[3]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

4
[ 174681-89-1 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: methyl 3-Phenylpyridine-2-carboxylate With sodium hydroxide In methanol at 20 - 50℃; for 18.5h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water Inert atmosphere;
31%	Stage #1: methyl 3-Phenylpyridine-2-carboxylate With sodium hydroxide In methanol at 20 - 50℃; for 19h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water at 20℃; Inert atmosphere;
	With sodium hydroxide In methanol at 20℃; for 1h;

Stage #1: methyl 3-Phenylpyridine-2-carboxylate With potassium hydroxide; water In ethanol at 50℃; for 2h; Stage #2: With phosphoric acid In ethanol; water

D To a solution of methyl 3-phenylpyridine-2-carboxylate (61.0 g, 286 mmol) in absolute ethanol was added potassium hydroxide (32.0 g, 572 mmol). After stirring at 5O0C for 2 h, the reaction mixture was cooled and adjusted to pH -7.5 with IM phosphoric acid. The mixture was diluted with water (1 L) and extracted with EtOAc (2 x 600 ml). The organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo to yield 3-phenylpyridine-2-carboxylic acid as a solid (54.7 g).

Reference： [1]Coomber, Charlotte E.; Porter, Michael J.; Aliev, Abil E.; Smith, Peter D.; Sheppard, Tom D. [Advanced Synthesis and Catalysis, 2020, vol. 362, # 22, p. 5105 - 5115]
[2]St. Laurent, Denis R.; Serrano-Wu, Michael H.; Belema, Makonen; Ding, Min; Fang, Hua; Gao, Min; Goodrich, Jason T.; Krause, Rudolph G.; Lemm, Julie A.; Liu, Mengping; Lopez, Omar D.; Nguyen, Van N.; Nower, Peter T.; O'Boyle, Donald R.; Pearce, Bradley C.; Romine, Jeffrey L.; Valera, Lourdes; Sun, Jin-Hua; Wang, Ying-Kai; Yang, Fukang; Yang, Xuejie; Meanwell, Nicholas A.; Snyder, Lawrence B. [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1976 - 1994]
[3]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]
[4]Current Patent Assignee: MERCK & CO INC - WO2008/36316, 2008, A2 Location in patent: Page/Page column 33

5
[ 103863-15-6 ]
[ 252002-18-9 ]
C₂₈H₃₁N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-phenylpyridine-2-carboxylic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.0833333h; Stage #2: 3-spiro[2,3-dihydro-1H-indene-1,4'-piperidine]-1-ylpropane-1-amine In chloroform at 20℃; for 0.5h;

Reference： [1]Goto, Yasuhiro; Arai-Otsuki, Sachie; Tachibana, Yukari; Ichikawa, Daisuke; Ozaki, Satoshi; Takahashi, Hiroyuki; Iwasawa, Yoshikazu; Okamoto, Osamu; Okuda, Shoki; Ohta, Hisashi; Sagara, Takeshi [Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 847 - 849]

6
[ 103863-15-6 ]
[ 1026682-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 4.2 g / polyphosphoric acid / Heating 2: zinc iodide / acetonitrile / 24 h / Heating 3: 4.6 g / HCl(gas) / 4 h / 20 °C

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

7
[ 103863-15-6 ]
[ 1026851-02-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 4.2 g / polyphosphoric acid / Heating 2: zinc iodide / acetonitrile / 24 h / Heating 3: 4.6 g / HCl(gas) / 4 h / 20 °C 4: 96 percent / hydrazine / 2 h / 20 °C

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

8
[ 103863-15-6 ]
9-trimethylsilanyloxy-9H-indeno[2,1-b]pyridine-9-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 4.2 g / polyphosphoric acid / Heating 2: zinc iodide / acetonitrile / 24 h / Heating

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

9
[ 103863-15-6 ]
1-(9-hydroxy-9H-indeno[2,1-b]pyridine-9-carbonyl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C 6.1: TFA / CH₂Cl₂ / 2 h / 20 °C

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

10
[ 103863-15-6 ]
1-(9-hydroxy-1-oxy-9H-indeno[2,1-b]pyridine-9-carbonyl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C 6.1: meta-chloroperoxybenzoic acid / CH₂Cl₂ / 0 - 20 °C 7.1: TFA / CH₂Cl₂

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

11
[ 103863-15-6 ]
[ 1026646-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

12
[ 103863-15-6 ]
[4-chloro-2-([1-(9-hydroxy-1-oxy-9H-indeno[2,1-b]pyridine-9-carbonyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4.2 g / polyphosphoric acid / Heating 2.1: zinc iodide / acetonitrile / 24 h / Heating 3.1: 4.6 g / HCl(gas) / 4 h / 20 °C 4.1: 96 percent / hydrazine / 2 h / 20 °C 5.1: HCl(gas); amyl nitrite / dimethylformamide; tetrahydrofuran / -20 °C / pH 1 - 2 5.2: 62 percent / N,N-diisopropylethylamine / dimethylformamide; tetrahydrofuran / 24 h / -20 °C 6.1: meta-chloroperoxybenzoic acid / CH₂Cl₂ / 0 - 20 °C

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]

13
[ 53636-56-9 ]
[ 103863-15-6 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2282 - 2293

14
[ 98-80-6 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / 1,4-bis(diphenylphosphino)butane; bis(benzonitrile)dichloropalladium; sodium carbonate / toluene / 18 h / Heating 2: NaOH / methanol / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 24 h / Reflux 2: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

Reference： [1]Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2282 - 2293]
[2]Current Patent Assignee: NANJING TOPTO SEMICONDUCTOR MATERIAL CO LTD - KR2020/108163, 2020, A

15
[ 103863-15-6 ]
[ 130944-00-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂ / Adams catalyst / acetic acid / 24 h / 2585.7 Torr 2: thionyl chloride / 1.) -10 to -15 deg C, 3 h, 2.) reflux, 12 h 3: 0.85 g / lithium aluminum hydride (LAH) / diethyl ether / 24 h

Reference： [1]Pillai; Nand [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 892 - 894]

16
[ 103863-15-6 ]
[ 130943-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Adams catalyst / acetic acid / 24 h / 2585.7 Torr 2: thionyl chloride / 1.) -10 to -15 deg C, 3 h, 2.) reflux, 12 h

Reference： [1]Pillai; Nand [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 892 - 894]

17
[ 19842-18-3 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 95 percent / H₂ / Raney Ni / ethanol / 2 h / 80 °C / 72400.7 Torr 2: 70 percent / 10percent Pd/C / 0.5 h / 300 - 310 °C 3: 84.5 percent / aq. KMnO₄ / 6 h / Heating

Reference： [1]Pillai; Nand [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 892 - 894]

18
[ 103863-15-6 ]
[ 847494-19-3 ]
C₃₁H₄₂BN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine In N,N-dimethyl-formamide at 0℃;

Reference： [1]Dorsey, Bruce D.; Iqbal, Mohamed; Chatterjee, Sankar; Menta, Ernesto; Bernardini, Raffaella; Bernareggi, Alberto; Cassarà, Paolo G.; D'Arasmo, Germano; Ferretti, Edmondo; De Munari, Sergio; Oliva, Ambrogio; Pezzoni, Gabriella; Allievi, Cecilia; Strepponi, Ivan; Ruggeri, Bruce; Ator, Mark A.; Williams, Michael; Mallamo, John P. [Journal of Medicinal Chemistry, 2008, vol. 51, # 4, p. 1068 - 1072]

19
[ 123-75-1 ]
[ 103863-15-6 ]
C₁₆H₁₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;

Reference： [1]Jin, Jian; Wang, Yonghui; Wang, Feng; Shi, Dongchuan; Erhard, Karl F.; Wu, Zining; Guida, Brian F.; Lawrence, Sarah K.; Behm, David J.; Disa, Jyoti; Vaidya, Kalindi S.; Evans, Christopher; McMillan, Lynette J.; Rivero, Ralph A.; Neeb, Michael J.; Douglas, Stephen A. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 9, p. 2860 - 2864]

20
[ 1131-48-2 ]
[ 7677-24-9 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-phenylpyridine N-oxide; trimethylsilyl cyanide With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride; sulfuric acid Heating; Further stages.;

Reference： [1]Jin, Jian; Wang, Yonghui; Wang, Feng; Shi, Dongchuan; Erhard, Karl F.; Wu, Zining; Guida, Brian F.; Lawrence, Sarah K.; Behm, David J.; Disa, Jyoti; Vaidya, Kalindi S.; Evans, Christopher; McMillan, Lynette J.; Rivero, Ralph A.; Neeb, Michael J.; Douglas, Stephen A. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 9, p. 2860 - 2864]

21
[ 103863-15-6 ]
(2S,2'S)-N,N'-(4,4'-((E)-ethene-1,2-diyl)bis(4,1-phenylene))dipyrrolidine-2-carboxamide dihydrochloride [ No CAS ]
[ 1429787-66-5 ]

Yield	Reaction Conditions	Operation in experiment
46.5%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

Reference： [1]St. Laurent, Denis R.; Serrano-Wu, Michael H.; Belema, Makonen; Ding, Min; Fang, Hua; Gao, Min; Goodrich, Jason T.; Krause, Rudolph G.; Lemm, Julie A.; Liu, Mengping; Lopez, Omar D.; Nguyen, Van N.; Nower, Peter T.; O'Boyle, Donald R.; Pearce, Bradley C.; Romine, Jeffrey L.; Valera, Lourdes; Sun, Jin-Hua; Wang, Ying-Kai; Yang, Fukang; Yang, Xuejie; Meanwell, Nicholas A.; Snyder, Lawrence B. [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1976 - 1994]

22
[ 62733-99-7 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 16 h / Reflux 3.1: sodium hydroxide / methanol / 19 h / 20 - 50 °C / Inert atmosphere 3.2: 20 °C / pH Ca_. 2 / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 2.1: dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 16 h / Reflux 3.1: sodium hydroxide / methanol / 19 h / 20 - 50 °C / Inert atmosphere 3.2: 20 °C / pH Ca_. 2 / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: triethylamine / 1 h / 0 - 20 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene / 1 h / 90 °C / Inert atmosphere 3.1: sodium hydroxide / methanol / 18.5 h / 20 - 50 °C / Inert atmosphere 3.2: pH 2 / Inert atmosphere

Reference： [1]St. Laurent, Denis R.; Serrano-Wu, Michael H.; Belema, Makonen; Ding, Min; Fang, Hua; Gao, Min; Goodrich, Jason T.; Krause, Rudolph G.; Lemm, Julie A.; Liu, Mengping; Lopez, Omar D.; Nguyen, Van N.; Nower, Peter T.; O'Boyle, Donald R.; Pearce, Bradley C.; Romine, Jeffrey L.; Valera, Lourdes; Sun, Jin-Hua; Wang, Ying-Kai; Yang, Fukang; Yang, Xuejie; Meanwell, Nicholas A.; Snyder, Lawrence B. [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1976 - 1994]
[2]St. Laurent, Denis R.; Serrano-Wu, Michael H.; Belema, Makonen; Ding, Min; Fang, Hua; Gao, Min; Goodrich, Jason T.; Krause, Rudolph G.; Lemm, Julie A.; Liu, Mengping; Lopez, Omar D.; Nguyen, Van N.; Nower, Peter T.; O'Boyle, Donald R.; Pearce, Bradley C.; Romine, Jeffrey L.; Valera, Lourdes; Sun, Jin-Hua; Wang, Ying-Kai; Yang, Fukang; Yang, Xuejie; Meanwell, Nicholas A.; Snyder, Lawrence B. [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1976 - 1994]
[3]Coomber, Charlotte E.; Porter, Michael J.; Aliev, Abil E.; Smith, Peter D.; Sheppard, Tom D. [Advanced Synthesis and Catalysis, 2020, vol. 362, # 22, p. 5105 - 5115]

23
[ 157865-84-4 ]
[ 103863-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 16 h / Reflux 2.1: sodium hydroxide / methanol / 19 h / 20 - 50 °C / Inert atmosphere 2.2: 20 °C / pH Ca_. 2 / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene / 1 h / 90 °C / Inert atmosphere 2.1: sodium hydroxide / methanol / 18.5 h / 20 - 50 °C / Inert atmosphere 2.2: pH 2 / Inert atmosphere

Reference： [1]St. Laurent, Denis R.; Serrano-Wu, Michael H.; Belema, Makonen; Ding, Min; Fang, Hua; Gao, Min; Goodrich, Jason T.; Krause, Rudolph G.; Lemm, Julie A.; Liu, Mengping; Lopez, Omar D.; Nguyen, Van N.; Nower, Peter T.; O'Boyle, Donald R.; Pearce, Bradley C.; Romine, Jeffrey L.; Valera, Lourdes; Sun, Jin-Hua; Wang, Ying-Kai; Yang, Fukang; Yang, Xuejie; Meanwell, Nicholas A.; Snyder, Lawrence B. [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1976 - 1994]
[2]Coomber, Charlotte E.; Porter, Michael J.; Aliev, Abil E.; Smith, Peter D.; Sheppard, Tom D. [Advanced Synthesis and Catalysis, 2020, vol. 362, # 22, p. 5105 - 5115]

24
[ 103863-15-6 ]
2-(2-(2-bromo-4-((methoxycarbonyl)amino)phenyl)-2-oxoethyl) 1-tert-butyl 3-phenylpiperidine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Adam’s catalyst; hydrogen / methanol / 20 °C 2: sodium hydrogencarbonate / acetone / 20 °C 3: caesium carbonate / 1,4-dioxane / 20 °C