Day: April 19, 2022

Related Products of 1187830-47-2, 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.1187830-47-2, name is 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine hydrochloride, molecular formula is C6H10ClN3, molecular weight is 159.62, as common compound, the synthetic route is as follows.

a) 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine.HCl (319 mg, 2 mmol) was combined with Boc2O (480 mg, 2.2 mmol) and K2CO3 (1.3 mL, 3 M aqueous, 2 equiv) in CH2Cl2 (10 mL). After 15 hours, the starting amine was consumed (LCMS). The reaction slurry was washed with brine and the organic layer was dried on MgSO4, filtered, and concentrated to give a viscous yellow oil (446 mg, 96%) that was used without further purification. MS: (ES) m/z calculated for C11H18N3O2 [M+H]+ 224.1, found 224.2.

Statistics shows that 1187830-47-2 is playing an increasingly important role. we look forward to future research findings about 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine hydrochloride.

Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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.1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, molecular weight is 218.02, as common compound, the synthetic route is as follows.

Step 4. (R,E)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide To a solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (10.93 g, 50.1 mmol) in THF (100 ml) was added (R)-(+)-2-methyl-2-propanesulfinamide (12.15 g, 100 mmol) and titanium (IV)-ethoxide (20.75 mL, 100 mmol). The resulting mixture was then heated at reflux for 1 h. The mixture was cooled to RT and brine (300 mL) was added. The mixture was stirred at RT for 15 min, then filtered and the solid was washed with DCM (2*100 mL). The organic layer was collected and the aqueous layer was dried over MgSO4 and concentrated. The residue was then dissolved in DCM (10 mL) and purified by silica gel chromatography, eluent 0%-100% EtOAc/hexane, to give 14.9 g of the title compound as a yellow solid. MS (ESI, positive ion) m/z: 321, 323 (M+H).

Statistics shows that 1111637-74-1 is playing an increasingly important role. we look forward to future research findings about 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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, Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate, blongs to pyridine-derivatives compound. Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate

49. Preparation of t-Butyl N-(4-Fluoro-2-methoxy-3-pyridinyl)carbamate To a solution of 8 g (35.7 mmol) of t-butyl N-(2-methoxy-3-pyridyl)carbamate in 200 mL of dry tetrahydrofuran was added with stirring at -60 C., 46.2 mL (78.5 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm slowly with stirring to -20 C. over a 20 to 30 min period. It was then cooled to about -60 C. and 12.2 g (38.7 mmol) of N-fluorodibenzenesulfonimide was added with stirring all at once. The mixture was allowed to warm to -20 C. and was poured into 500 mL of ether. The resulting ethereal solution was washed with a mixture of 2.5 g (41.7 mmol) of acetic acid and 150 mL of water. The aqueous phase was extracted with 200 mL of ether. The ethereal extracts were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by flash chromatography to obtain 6.7 g (77 percent of theory) of the title compound as a colorless solid melting at 75-77 C. Elemental Analysis C11 H15 FN2 O3 Calc.: %C, 54.5; %H, 6.24; %N, 11.6 Found: %C, 54.2; %H, 6.39; %N, 11.4 1 H NMR (CDCl3): 7.88 (dd, 1H, j=5.8, 7.6); 6.68 (dd, 1H, j=5.8, 8.9); 5.9 (br, 1H); 3.9 (s, 3H); 1.45 (s, 9H).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139585-48-1, 2-Chloro-5-methoxypyridine, 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, name: 2-Chloro-5-methoxypyridine, blongs to pyridine-derivatives compound. name: 2-Chloro-5-methoxypyridine

5) 2-Hydrazino-5-methoxypyridine; A solution of the2-chloro-5-methoxypyridine (4.0 g) in hydrazine monohydrate (30 ml) was stirred at 100C for 24 hours. After cooling with air, the reaction solvent was evaporated under reduced pressure. To the residue was added chloroform and 1N aqueous sodium hydroxide and the phases were separated. The organic layer was dried over anhydrous magnesium sulfate. After filtration,_the solvent was evaporated under reduced pressure to give 2-hydrazino-5-methoxypyridine (705 mg, 18%) as an oily product. LC-MSm/z: 140 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698626; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

Intermediate S-9 sodium 2-methoxy- -(trifluoromethyl)pyridine-4-thiolate Step a: To a -78 C solution of diisopropylamine (0.966 mL, 6.77 mmol) in THF (20 mL) was added ra-BuLi (1.6 M in hexanes, 4.23 mL, 6.77 mmol) dropwise and the reaction mixture was stirred for 5 min at -78 C. A solution of 2-methoxy-3- (trifluoromethyl)pyridine (1.2 g, 6.77 mmol) in THF (10 mL) was added and the resulting mixture was stirred for 2 h at -78 C. I2 (1.72 g, 6.77 mmol) in THF (5 mL) was added at -78 C and the resulting mixture was allowed to warm to RT within 30 min and was further stirred at this temperature for 30 min. The volatiles were removed under reduced pressure, the residue was dissolved in Et20 (200 mL) The organic layer was washed sequentially with sat. aq. Na2S2( (200 mL), sat. aq. NH4CI (200 mL), and sat. aq. NaHC03 (200 mL), dried over MgS04, filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to give 4-iodo-2-methoxy-3- (trifluoromethyl)pyridine (540 mg, 1.354 mmol). MS m/z, 304.0 (M+H)+.

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; FORTANET, Jorge Farcia; JOUK, Andriana; KARKI, Rajesh; LAMARCHE, Matthew J.; LIU, Gang; PALERMO, Mark G.; PEREZ, Lawrence Blas; SARVER, Patrick James; SHULTZ, Michael David; SENDZIK, Martin; TOURE, Bakary-Barry; YU, Bing; (173 pag.)WO2016/203406; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2546-56-7 ,Some common heterocyclic compound, 2546-56-7, molecular formula is C5H3ClFN, 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.

[00408] Intermediate 101 A. 2-Bromo-4-chloro-3-fluoropyridine: To a solution of 2,2,6, 6-tetramethylpiperidine (1.54 mL, 9.12 mmol) in THF (40 mL) was added 1.6 Mu kappa- BuLi in hexanes (5.23 mL, 8.36 mmol) dropwise at -78 C. The resulting solution was stirred for 0.5 h at 0 C. It was then cooled to -78 C and 4-chloro-3-fluoropyridine (0.769 mL, 7.60 mmol) in 5 mL THF was added dropwise over 30 min. The resulting solution was stirred at -78 C for 30 min. To the solution was added NBS (1.624 g, 9.12 mmol) in THF (25 mL) dropwise and the resulting solution was stirred for 1 h at -78 C, then at ambient temperature for 12 h. The reaction mixture was then diluted with EtOAc and water. The organic layer was washed with brine, concentrated and purified on silica gel chromatography to give the desired product (0.541 g, 34%) as orange oil (volatile). 1H NMR (400 MHz, CDC13) delta 8.13 (d, J = 5.0 Hz, 1H), 7.35 (t, J = 5.1 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2546-56-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14916-65-5, 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. 14916-65-5, name is 6-Nitropyridin-3-amine, molecular formula is C5H5N3O2, 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.

Intermediate V-1 was synthesized through the reaction of 5-amino-2-nitropyridine with sodium azide and orthoformate and subsequent reduction with hydrogen in the presence of palladium hydroxide/activated carbon

According to the analysis of related databases, 14916-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; EBISAWA, Masaru; TAKEUCHI, Susumu; MINAMIZONO, Kunio; SASAKI, Kosuke; YOKOSAKA, Takuya; IGARASHI, Junji; MARUYAMA, Akinobu; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (447 pag.)EP3305785; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 845306-04-9, Adding some certain compound to certain chemical reactions, such as: 845306-04-9, name is 6-Chloro-N-methylpicolinamide,molecular formula is C7H7ClN2O, 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 845306-04-9.

In a pressure tube, argon was bubbled through a suspension of 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one (50 mg, 197 muiotaetaomicron, Eq: 1, WO2014/202493 Al), 6-chloro- N-methylpicolinamide (40.4 mg, 237 muiotaetaomicron, Eq: 1.2) and cesium carbonate (83.6 mg, 257 muiotaetaomicron, Eq: 1.3) in dioxane (987 mu) for 5 minutes. Xantphos (22.8 mg, 39.5 muiotaetaomicron, Eq: 0.2) and tris(dibenzylideneacetone)dipalladium (0) (36.2 mg, 39.5 muiotaetaomicron, Eq: 0.2) were added and the reaction mixture was heated to 120 C for 1 day under argon. The residue was evaporated in vacuo and purified by chromatography on silica gel, followed by prep HPLC to afford the desired product as a light yellow solid (45 mg, 58 ). MS (m/z) = 388.2 [M + H]+.

According to the analysis of related databases, 845306-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GAUFRETEAU, Delphine; KOLCZEWSKI, Sabine; PLANCHER, Jean-Marc; STOLL, Theodor; HALM, Remy; (85 pag.)WO2017/76852; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1003711-43-0, 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.1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

(A) To an ice-cooled solution of 6-bromo-5-methylpyridin-3-ol (500 mg, 2.66 mmol) in DMF (10 mL) was added NaH (60% wt; 160 mg, 4.0 mmol) in a portionwise fashion and the resultant mixture was allowed to stir at rt for 1h. The mixture was then cooled to 0 C and CH3I (755 mg, 5.32 mmol) was added in dropwise fashion. After stirring for 1 h at rt, the reaction was quenched with water (20 mL) and the mixture was extracted with EtOAc (3 x 30 mL). The combined extracts were dried (Na2SO4), concentrated under reduced pressure and purified by silica gel chromatography (0-10% EtOAc/petroleum ether) to afford 2-bromo-5-methoxy-3- methylpyridine (400 mg, 74% yield) as a white solid. LC/MS: mass calcd. for C7H8BrNO: 202.05, found: 202.0, 204.0 [M, M+2]+.

The chemical industry reduces the impact on the environment during synthesis 1003711-43-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; KUO, Gee-Hong; PLAYER, Mark R.; YANG, Shyh-Ming; ZHANG, Yue-Mie; HUANG, Hui; (260 pag.)WO2016/57731; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, 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, Application In Synthesis of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate

To a stirring solution of methyl 1 H-pyrazolo[3,4-c]pyridine-5-carboxylate (0.628 g, 3.545 mmol) in DMF (15 mL) was added 4-fluorobenzyl bromide (0.442 mL, 3.545 mmol) followed by potassium carbonate (0.490 g, 3.545 mmol), and the mixture was stirred overnight at room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The crude solid was purified by flash column chromatography (silica gel, 0-20% acetonitrile: chloroform v/v) to provide pure desired methyl 1-(4-fluorobenzyl)-iH-pyrazolo[3,4-c]pyridine-5-carboxylate (0.66 g, 30% yield over three steps) and the undesired methyl 2-(4-fluoro-benzyl)-2H-pyrazolo[3,4-c]pyridine-5- carboxylate (0.73 g, 33% yield) as white solids. Methyl 1-(4-fluorobenzyl)-lH-pyrazolo[3,4- c] pyridine-5-carboxylate: (at)HNMR (CDCI3, 300 MHz) 8 ppm 8.91 (s, 1 H), 8.59 (s, 1 H), 8.22 (s, 1 H), 7.26 (m, 2H), 7.02 (m, 2H), 5.69 (s, 2H), 4.03 (s, 3H). LCMS (API-ES M+H+) 286. Methyl 2-(4- fluoro-benzyl)-2H-pyrazolo [3,4-c]pyridine-5-carboxylate: ‘HNMR (CDCI3, 300 MHz): 8 ppm 9.32 (s, 1 H), 8.51 (s, 1 H), 8.10 (s, 1 H), 7.36 (m, 2H), 7.09 (m, 2H), 5.65 (2H, s), 4.02 (s, 3H). LCMS (API-ES M+H+) 286.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem