Category: pyridine-derivatives

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

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

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

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

Related Products of 139022-25-6 , The common heterocyclic compound, 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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.

[0227] Step 5A. (R)-N- [[4-(3 ,5-difluorophenyl)sulfinylphenyll methyll imidazo [1,2- alpyridine-6-carboxamide. A solution of imidazo[1,2-a]pyridine-6-carboxylic acid (100 mg, 0.62 mmol, 1.50 equiv), EDCI (94.7 mg, 0.49 mmol, 1.20 equiv), HOBt (67 mg, 0.50 mmol,1.20 equiv), and diisopropylethylamine (160 mg, 1.24 mmol, 3.00 equiv) in DMF (10 mL) was stirred at 25 C for 30 mi [4-[(R)-(3,5-Difluorobenzene)sulfinyl]phenyl]methanamine (110 mg, 0.41 mmol, 1.00 equiv) was then added and the resulting solution was stirred for 12 h at 25 C. The reaction mixture was quenched with 50 mL of water. The resulting mixture was extracted with 2×50 mL of dichloromethane. The combined organic layers were washed with lxi 00 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (100/5) to give 35 mg (2 1%) of the title compound as a white solid. Chiral HPLC, Column: CHIRALPAK AD-H, Column size: 0.46*25 cm, 5 um, Mobile phase: Hexane/EtOH = 50/50 (0.1% TEA), Flow: 1.0 mL/min, Pressure: 5.0 MPa, Detector: UV-254 nm, Temperature: 25C, RT = 11.4 mi LC/MS (Method B, ESI): RT = 1.98 mi m/z = 412.1 [M+Hf?. ?H NMR (400 MHz, CD3OD) oe 9.04 (s, 1H), 7.96 (s, 1H),7.75 (d, J = 8.4 Hz, 2H), 7.71 (s, 1H), 7.66 (s, 1H), 7.59 (m, 3H), 7.35 (d, J = 4.8 Hz, 2H),7.10 (m, 1H), 4.66 (s, 2H). ?9F NMR (400 MHz, CD3OD) oe: -108.1.

The synthetic route of 139022-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73027-79-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 73027-79-9, name is 4,6-Dichloronicotinic acid. A new synthetic method of this compound is introduced below.

4,6-Dichloro-nicotinic acid (10.3 g, 53.4 mmol) was suspended in CH2Cl2 (200 mL). Oxalyl chloride (14 mL, 158 mmol) was added and the reaction was placed in an ice bath. DMF (1.0 mL) was added and the reaction was fitted with an air cooled condenser. The reaction was stirred for 3 h and allowed to warm to 25 C. The volatiles were removed in vacuo and the crude residue was resuspended in THF (200 mL) and cooled to 0 C. To this stirred suspension was added concentrated aqueous ammonia (75 mL) dropwise and the reaction was allowed to stir for 1 h. The volatiles were removed and the crude was redissolved in EtOAc and poured into brine. The aqueous phase was separated and extracted twice with EtOAc. The organic layers were combined, dried (Na2SO4), decanted and concentrated to afford 4,6-dichloro-nicotinamide as a beige solid (7.27 g, 71%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73027-79-9, 4,6-Dichloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/217417; (2006); 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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.COA of Formula: C6H3F2NO2

Synthesis of 3-Butyl-5-fluoro-isonicotinic acid [A067] 3,5-Difluoro-isonicotinic acid (0.557 g, 3.5 mmol) was suspended in anhydrous THF (8 mL) at 0C, under an atmosphere of nitrogen. To this was added butyl magnesium chloride (2.0 M in diethyl ether, 5.25 mL, 10.5 mmol) dropwise over 10 minutes. The suspension slowly changed form during the slow addition with preliminary agglomeration of solid then the solid started to dissolve slowly, achieving full solution around completion of addition of reagent. The reaction mixture was allowed to warm to room temperature and stirred over 72 hours to form a thick yellow suspension. Diluted with water and transferred into a single neck flask and concentrated in vacuo. The yellow solid was diluted with water (10 mL) and EtOAc (10 mL). The pH was adjusted pH~2, by dropwise addition of HC1 (cone.) and extracted with EtOAc (x3 – some of the yellow colour goes into organics). Combined organics were washed with brine (xl), dried (MgSC^) and concentrated in vacuo to yield the title compound [A067] as an orange gum/solid (0.402g) that solidifies slowly: NMR: (1H, 300MHz, d6-dmso); 8.52 (1H, s), 8.42 (1H, s), 2.67 (2H, t), 1.58-1.48 (2H, m), 1.35-1.22 (2H, m), 0.87 (3H, t); LCMS method: 1, RT: 1.22 min, MI 198 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,903522-29-2, 3,5-Difluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; CEPHALON, INC.; CANCER RESEARCH TECHNOLOGY LIMITED; BRESLIN, Henry, J.; DORSEY, Bruce, D.; DUGAN, Benjamin, J.; FOWLER, Katherine, M.; HUDKINS, Robert, L.; MESAROS, Eugen, F.; MONCK, Nathaniel, JT; MORRIS, Emma, L.; OLOWOYE, Ikeoluwa; OTT, Gregory, R.; PAVE, Gregoire, A.; ROFFEY, Jonathan, R. A.; SOUDY, Christelle, N.; TAO, Ming; ZIFICSAK, Craig, A.; ZULLI, Allison, L.; WO2014/52699; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 590371-58-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 590371-58-7, name is 3-Bromo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-2-(trifluoromethyl)pyridine (1.0 g, 4.42 mmol), XantPhos (256 mg, 0.442 mmol), Pd2(dba)3 (203 mg, 0.221 mmol) in dioxane (12 mL) was added (at RT and under N2) 2-ethylhexyl-3-mercaptopropanoate (1.1 mL, 4.87 mmol) followed by addition of DIPEA (1.55 mL, 8.85 mmol). The resulting solution was stirred in a microwave reactor for 1 h at 110 C. After cooling to RT, the reaction was filtered through a pad of Celite followed by EtOAc (25 mL) wash. The combined filtrates were concentrated and the resulting residue was purified by silica chromatography (0 to 30% gradient of EtO Ac/heptane) to give 2-ethylhexyl 3-((2-(trifluoromethyl)pyridin-3-yl)thio)propanoate (1.41 g, 3.88 mmol). MS m/z 364.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,590371-58-7, 3-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; CHEN, Christine Hiu-tung; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KARKI, Rajesh; KATO, Mitsunori; LAMARCHE, Matthew J.; PEREZ, Lawrence Blas; SMITH, Troy Douglas; WILLIAMS, Sarah; GIRALDES, John William; TOURE, Bakary-barry; SENDZIK, Martin; WO2015/107495; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79055-62-2 ,Some common heterocyclic compound, 79055-62-2, molecular formula is C6H7ClN2, 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.

To a mixture of tert-butyl nitrite (150 mL, 1262 mmol) in acetonitrile (1000 mL) was added copper(II) bromide (226 g, 1010 mmol) at 30 C. The solution was then stirred at 22 C for 40 min and then cooled to 0 C. A solution of 2-chloro-5-methylpyridin-4-amine (120 g, 842 mmol) in acetonitrile (500 mL) was added at 0 C. The reaction was stirred at 0 C for 1 h and then warmed to 22 C and stirred for 12 h. The resulting mixture was concentrated in vacuum. The residue was dissolved in DCM (2000 mL), washed with aqueous NH3 (15%, 2000 mL), dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuum and the resulting residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give 4-bromo-2-chloro-5-methylpyridine as colorless oil. MS: 206 / 208 (M + 1 / M + 3). 1H MR (400 MHz, CDC13) delta 8.14 (s, 1H), 7.48 (s, 1H), 2.30 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,79055-62-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 181123-11-5, name is 5-Chloro-2-cyano-3-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 181123-11-5

To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H).

The synthetic route of 181123-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem