Day: June 11, 2021

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 69722-29-8, name is Ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, molecular formula is C11H12N4O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. SDS of cas: 69722-29-8

Reference Example 2-64 1-(2-Pyridinyl)-1H-pyrazol-5-ylamine A suspension of ethyl 5-amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate (27.9 g, 120 mmol) in 4N sodium hydroxide (300 mL) was heated under reflux for 1 hour. The suspension was allowed to cool to room temperature, neutralized by the addition of conc. hydrochloric acid, and further made acidic by the addition of acetic acid. The resulting crystals were collected by filtration, washed with ethanol, and air dried. The crystals thus obtained were subjected to heat at 200 C., and washed with diethylether to give the title compound (6.02 g, 31% yield). NMR (CDCl3) delta: 5.51 (1H, d, J=1.8 Hz), 5.95 (2H, br s), 7.07-7.13 (1H, m), 7.42 (1H, d, J=1.8 Hz), 7.75-7.84 (1H, m), 7.98 (1H, d, J=8.4 Hz), 8.33 (1H, dd, J=1.6 Hz, 4.6 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 69722-29-8.

Reference:
Patent; Uchikawa, Osamu; Mitsui, Keita; Asakawa, Akiko; Morimoto, Shigeru; Yamamoto, Masataka; Kimura, Hiroyuki; Moriya, Takeo; Mizuno, Masahiro; US2003/187014; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 800401-67-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 800401-67-6, name is Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate, molecular formula is C10H9ClN2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Route A: To a solution of 5-chloro-lH-pyrrolo [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 17,1. 78g, 7. 9MMOL) in ethanol (70mL) was added sodium hydroxide solution (5.2mL, 2M, 10. 3MMOL) and the mixture heated under reflux for 2h. The solvent was removed in vacuo and the solid dissolved in water (150ML) and acidified to pH 4 with acetic acid to give the title compound as a brown solid that was isolated by filtration. ON (CD30D): 7.13 (1H, s), 7.68 (1H, s), 8. 58 (1H, s); M/Z (ES+) =197 [M+H] +

According to the analysis of related databases, 800401-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98400-69-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 98400-69-2, name is 4-(Boc-Amino)pyridine, molecular formula is C10H14N2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of BL (12 g, 0.06 mol) in dry THF (200 mL) under inert atmosphere was added n-butyl lithium (79.12 mL, 0.18 mol) at -78 C. The reaction was warmed to 0 C and stirred for 30 min. Carbon dioxide gas was added to the reaction mass at -78 C for 1 h, then at RT for 1 h. The reaction was monitored by TLC. After complete consumption of the starting material, the reaction mass was diluted with water (200 mL) and washed with diethyl ether (2×150 mL). The aqueous layer was acidified with citric acid to pH~4. The obtained solid was filtered and dried under vacuum to afford BM (5.1 g, 35%) as a white solid. *H NMR (400 MHz, DMSO-i: delta 11.76 (br s, 1H), 8.96 (s, 1H), 8.52 (d, / = 15.0 Hz, 1H), 8.22 (d, / = 15.0 Hz, 1H), 1.49 (s, 9H).

According to the analysis of related databases, 98400-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, William, J.; YATES, Christopher, M.; RAFFERTY, Stephen, W.; WO2014/117090; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 55758-32-2, name is 6-Fluoropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-Fluoropyridin-3-ol

Preparation 17; 2-Fluoro-5-methoxymethoxy -pyridine; Add 6-fluoro-pyridin-3-ol (3.5 g, 30.95 mmol) to a suspension of sodium hydride (1.49 g, 37.14 mmol) in dimethylformamide (20 mL). Stir the mixture for 1 hour. Add chloromethyl methyl ether (2 g, 25.0 mmol). Stir the mixture at room temperature overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with water and saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to brown oil. Purify by column chromatography (10 % ethyl acetate in hexane) to afford the title compound (4.30 g, 88.4 %) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 3.48 (s, 3H), 5.15 (s, 2H), 6.85 (dd, J= 3.6 Hz, J= 8.8 Hz, IH), 7.47 (m, 1 H), 7.96 (m, IH).

With the rapid development of chemical substances, we look forward to future research findings about 55758-32-2.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.96568-04-6, name is Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, molecular formula is C10H8Cl2FNO3, molecular weight is 280.08, as common compound, the synthetic route is as follows.Safety of Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate

Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (19.5 g, 69.6 mmol) and triethyl orthoformate (23.1 ml, 140 mmol) were initially charged in acetic anhydride (46 ml, 490 mmol) and the mixture was stirred at 140 C. overnight. The reaction mixture was then concentrated under reduced pressure and reacted further in the subsequent steps without further work-up. Quantitative conversion was assumed. LC-MS (Method 1): Rt=1.00 min; MS (ESIpos): m/z=336 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96568-04-6, Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; VAKALOPOULOS, Alexandros; BOULTADAKIS ARAPINIS, Melissa; STRAUB, Alexander; TINEL, Hanna; BRECHMANN, Markus; WITTWER, Matthias Beat; KULLMANN, Maximilian Andreas; FREUDENBERGER, Till; MONDRITZKI, Thomas; MARQUARDT, Tobias; (165 pag.)US2019/263805; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 107504-08-5, Adding some certain compound to certain chemical reactions, such as: 107504-08-5, name is 5-Fluoro-2-picolinic acid,molecular formula is C6H4FNO2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 107504-08-5.

In the ice bath,To a solution of 5-fluoro-2-pyridinecarboxylic acid (10 g) in methanol was slowly added dropwise thionyl chloride (10.3 mL).Dripping is completed.After moving to 80C for 8 hours,Cool to room temperatureMethanol was distilled off under reduced pressure.Diluted with ethyl acetate,In the ice bath,Saturated sodium bicarbonate solution was added to the reaction mixture,Adjust pH = 8 or so.Extract with ethyl acetate,The combined organic phases are washed with saturated brine,Dried over anhydrous sodium sulfate,Filter and concentrate the filtrate in vacuoThe residue was separated by silica gel column chromatography to give the title compound (9.895 g).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 107504-08-5, 5-Fluoro-2-picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.88912-27-0, name is 3-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.Product Details of 88912-27-0

A mixture of 0.35 g of 2-amino-4-trifluoromethoxy phenol, 0.29 g of 3- chloroisonicotinic acid, 1.04 g of (benzotriazole-l-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (hereinafter, referred to as a BOP reagent), 0.24 g of triethylamine and 5 ml of DMF was stirred at room temperature for two hours. Water was added to the reaction mixture, precipitated solid was collected by filtration. The resultant solid was dissolved in ethyl acetate. Then, the organic layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was subjected to silica gel column chromatography to give 0.43 g of 3-chloro- N-[2-hydroxy-5-(trifluoromethoxy)phenyl]isonicotinamide.-NMR (DMSO-d6) delta: 10.37 (br s, 1H), 10.15 (br s, 1H), 8.75-8.73 (m, 1H), 8.64-8.61 (m, 1H), 8.04-8.01 (m, 1H), 7.63-7.60 (m, 1H), 7.07-7.02 (m, 1H), 6.98-6.94 (m, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-27-0, 3-Chloroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49220; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 799293-83-7, 3-Bromothieno[3,2-c]pyridin-4(5H)-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 3-Bromothieno[3,2-c]pyridin-4(5H)-one, blongs to pyridine-derivatives compound. Safety of 3-Bromothieno[3,2-c]pyridin-4(5H)-one

Step-1: (0216) (0217) Preparation of 3-(4-chloro-3-(trifluoromethyl)phenyl)thieno[3,2-c]pyridin-4(5H)-one: (0218) [00115] To a solution of 3-bromothieno[3,2-c]pyridin-4(5H)-one (0.55 g, 2.17 mmol) and (4-chloro-3-(trifluoromethyl)phenyl)boronic acid (0.73 g, 3.25 mmol) in 1,4-dioxane:water mixture (20 mL, 4:1), potassium carbonate (0.9 g, 6.51 mmol) was added. The reaction mixture was purged with argon for 15 minutes and PdCl2(PPh3)2 (0.15 g, 0.21 mmol) was added. Then the reaction mixture was stirred at 100 C for 18 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel column chromatography using 30% ethyl acetate in hexane to afford the title compound 3-(4-chloro-3-(trifluoromethyl)phenyl)thieno[3,2-c]pyridin-4(5H)- one (0.74 g, 94% yield) as off-white solid. Calculated (M+H): 330; Found (M+H): 330.0.

The synthetic route of 799293-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 875781-17-2 , The common heterocyclic compound, 875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine (99 mg, 0.5 mmol), bis(pinacolato)diboron (152mg, 0.6 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (36.5 mg, 0.05 mmol) and potassium acetate (98 mg, 1 mmol) in 1,4-dioxane (5 mL) was degassed and stirred at 100 C under Argon atmosphere for 3 hrs. To the reaction mixute was added compound 8b (100 mg, 0.31 mmol), potassium carbonate (276 mg, 2 mmol) and water (1 mL). The resulting mixture was degassed and stirred at 100 C under Argon atmosphere for 3 hrs. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol/ammonium water 600:10:1, v/v) to give the title compound 9i (50 mg, 28% yield for two steps) as a yellow solid.

The synthetic route of 875781-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Songwen; Han, Fangbin; Liu, Peng; Tao, Jing; Zhong, Xuechao; Liu, Xiujie; Yi, Chongqin; Xu, Heng; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 790 – 793;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 54903-50-3, name is 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine, molecular formula is C7H9NS, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. name: 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine

To a stuffing solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (5.6 g, 40.3 mmol), and Et3N (6.1 g, 60.4 mmol) in MeOH (100 mL) was added Boc2O (10.5g, 48.4 mmol) in 30 mm at 0 C. The mixture was stuffed at 20 C for 16 hours. The reaction mixture was concentrated after the starting material was consumed and the residue re-dissolved in DCM, the organic solution washed with water and aq. HC1 (0.5 M), the organic phases was dried and concentrated to give 8.9 g (yield: 92.4%) of tert-butyl 6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxylate as white solid. ?H NMR (400MHz, CDC13) (ppm): 7.14 (d, 1=5.0 Hz, 1H), 6.81 (d, 1=5.0 Hz, 1H), 4.52 (br. s, 2H), 3.75 (br. s, 2H), 2.87 (br. s, 2H), 1.51 (s, 9H). LCMS (mlz): 240.2 [M+H]

With the rapid development of chemical substances, we look forward to future research findings about 54903-50-3.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; SHAPIRO, Gideon; (393 pag.)WO2015/200677; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem