Pyridine-derivatives

Electric Literature of 130473-27-7, 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. 130473-27-7, name is 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, molecular formula is C8H6N2O2, 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 ethyl 1 H-pyrrolo [2,3-c] PYRIDINE-5-CARBOXYLATE [prepared according to M. Dekhane, P. Potier, R. H. Dodd, Tetrahedron, 1993,49, 8139-8146] (0.50 G, 2.63 MMOL) in DMF (10 mL) under a nitrogen atmosphere was added sodium hydride (0.087 g, 80% in mineral oil, 2.89 mmol) and 2, 4-difluorobenzyl bromide (0. 60g, 2.89 mmol). The resulting mixture was stirred for 16 hours at ambient temperature. It was quenched with water (30 ML}, and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were washed with water (2 x 30 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Elution with hexane: ethyl acetate (1: 1) provided the title compound as a light yellow solid (0.40 g, 48% YIELD). 1 H NMR (CD3OD) #; 8.86 (s, 1 H), 8.47 (s, 1 H), 7.71 (d, 1 H, J = 3. 2Hz), 7.31 (dd, 1 H, J = 6. 3Hz), 6.94-7. 05 (m, 2H), 6.79 (d, 1 H, J = 3.2Hz), 5.63 (s, 2H), 4.46 (q, 2H, J = 7.3Hz), 1.45 (t, 3H, J = 7.3Hz). LCMS (API-ES, M+H+) : 317.0.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 130473-27-7, 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid.

Reference:
Patent; PFIZER INC.; WO2004/39803; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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.

Example 325e 5-Bromo-1,3-dimethyl-1H-pyrazolo[3,4-c]pyridine 325e and 5-Bromo-2,3-dimethyl-2H-pyrazolo[3,4-c]pyridine 326a A mixture of 325d (3.0 g, 14.2 mmol), CH3I (2.40 g, 17.0 mmol), and K2CO3 (2.9 g, 21.3 mmol) in acetonitrile (60 mL) was stirred at 30C for 1 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 8:1 petroleum ether/ethyl acetate to afford 325e (920 mg, 29.0%) as a white solid, and eluting with 2:1 petroleum ether/ethyl acetate to afford 326a (390 mg, 12.0%) as a gray solid. MS-ESI: [M+H]+ 226.1.

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 31181-88-1, name is 5-Fluoropicolinaldehyde. A new synthetic method of this compound is introduced below., SDS of cas: 31181-88-1

a) 2-Ethynyl-5-fluoro-pyridine To a mixture of 5-fluoro-2-formylpyridine (1.10 g, 9.0 mmol) in MeOH (38 mL) was added potassium carbonate (2.44 g, 0.018 mol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.03 g, 11 mmol) in MeOH (12 mL). The mixture was stirred at room temperature for 90 min, then extracted with diethylether. The organic layers were then washed with sodium hydrogen carbonate solution (1 M) and brine, dried over sodium sulfate, filtered and evaporated at to give the title compound (1.01 g, 78%) as a light brown liquid. MS: m/e=121.0 [M]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 31181-88-1, 5-Fluoropicolinaldehyde.

Reference:
Patent; Hernandez, Maria-Clemencia; Lucas, Matthew C.; Thomas, Andrew; US2012/115844; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 145255-19-2, 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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide, molecular formula is C6H7N3O, 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 solution of 2,4-dichloro-6-fluoro-benzoyl chloride (2.5 g, 11.0 mmol) and DIEA (4.8 mL, 27 mmol) in 1 -methyl -pyrrolidin-2 -one (25 mL) at 0 C was added a solution of 5-aminopyridine-2- carboxamide (1.51 g, 11.0 mmol) in dichloromethane (12.5 mL) dropwise. The reaction was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was diluted with water (20 mL) and the resulting suspension was filtered to provide 5-[(2,4-dichloro-6-fluoro-benzoyl)amino]pyridine-2- carboxamide (1.2 g, 33%). ESI-MS m/z calc. 326.99, found 328.1 (M+l)+; retention time (Method B): 1.16 minutes (3 minute run). NMR (400 MHz, DMSO-d6) delta 11.34 (s, 1H), 8.88 – 8.82 (m, 1H), 8.29 (dd, J = 8.5, 2.5 Hz, 1H), 8.12 – 8.01 (m, 2H), 7.76 (dq, J = 4.2, 2.0 Hz, 2H), 7.58 (s, 1H) ppm.

According to the analysis of related databases, 145255-19-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67938-76-5 ,Some common heterocyclic compound, 67938-76-5, 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.

The compound 2-(aminomethyl)-5-chloropyridine (18 g, 0.13 mol) was dissolved in dichloromethane (50 mL) and hydrochloric methanol solution (5 M, 50 mL) was added. After stirring for several min a white solid began to precipitate. The mixture was stirred for 1 h at 0-5 °C, and the solid was collected by filtration and the filtrate was evaporated in vacuo to give some off-white solid. The combined solid was washed with a small amount of cold DCM. The product was dried in vacuo to yield the indicated compound as the hydrochloric salt. 1H-NMR (d6-DMSO, 400 MHz) delta 8.70 (s, 3H), 8.62 (s, 1H), 8.0 (dd, J=2.5, 6 Hz, 1H), 7.60 (d, J=8.5 Hz, 1H), 4.15 (m, 2H).

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. 67938-76-5, (5-Chloropyridin-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; BROCKUNIER, Linda, L.; GUO, Jian; PARMEE, Emma, R.; RAGHAVAN, Subharekha; ROSAUER, Keith; STELMACH, John, E.; SCHMIDT, Darby Rye; (87 pag.)EP2373317; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-Amino-6-chloropyridine-2-carboxylic acid

3-amino-6-chloro-pyridine-2-carboxylic acid (95 mg, 0.55 mmol) is taken up in THF (1 mL) and combined with BH3-THF complex (2.2 mL, 2.2mmol, 1 M in THF). The reaction mixture is stirred for 2 d at 200C. The reaction is ended with dilute HCl and H2O, then neutralised with NaHCO3, extracted with EtOAc, the organic phase is dried on MgSO4, the solvent is eliminated in vacuo and (3-amino-6-chloro-pyridin-2-yl)-methanol is obtained (HPLC-MS: tRet. = 0.79 min, MS(M+H)+ = 159; method AFEC).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 866807-27-4, 3-Amino-6-chloropyridine-2-carboxylic acid.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; McCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7114; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 82523-07-7, 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.82523-07-7, name is Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate, molecular formula is C8H7N3O2, molecular weight is 177.16, as common compound, the synthetic route is as follows.

5 g (28.22 mmol) of 3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester was dissolved in 40 mL of NaOH aqueous solution (2M) under ice-cooling.After 4 h of reaction, the reaction mixture was adjusted to pH 7 with dilute hydrochloric acid (2M). Allow to stand and allow the solid to be analyzed. Filter, filter and wash with distilled water, dry, yield 1.757 g (38%) of the title compound. It is a pale yellow solid.

The chemical industry reduces the impact on the environment during synthesis 82523-07-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Capital University of Medical Sciences; Zhao Ming; Peng Shiqi; Wang Yuji; Wu Jianhui; Gui Lin; Wang Yongjian; (12 pag.)CN108976226; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1167056-96-3, 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 1167056-96-3, name is 3-Bromo-5-chloro-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 3-bromo-5-chloro- 1H- pyrrolo[2,3-c]pyridine (AJ-2) (2.9 g, 12.6 mmol) in anhydrous DMF (100 mL) was added 2- chloro-6-(trifluoromethyl)benzoyl chloride (4.6 g, 18.9 mmol) and NaH (60%) (1 g, 25.2 mmol). The solution was stirred at room temperature for 2 hours. The solution was quenched with H2O(400 mL). The suspension was extracted with EtOAc (150 mL x 3). The combined organic layer was washed with H2O(100 mL x 2) and brine (100 mL x 2) and dried over anhydrous Na2SO4. The solution was evaporated and dried over vacuo and 5.7 g product was obtained. LCMS (ESI) calc?d for C15H6BrCl2F3N2O [M+H]+: 437, found: 437.

According to the analysis of related databases, 1167056-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan; WO2014/28589; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

General procedure: To a 0.5 M solution of 2-chloro-5-cyanopyridine (10 mmol) in isopropyl alcohol hydrazine hydrate (50 mmol) was added in portions over 1 hour. The reaction mixture was heated at reflux for 24 hours, cooled down to ambient temperature and the resulting precipitate of 5-cyano-2-hydrazinopyridine was separated by filtration, washed with isopropyl alcohol and air-dried. Without further purification, it was dissolved in the respective aliphatic carboxylic acid (0.5M) and heated at reflux for 48 hours. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was triturated with 1M aqueous sodium bicarbonate. The precipitate thus formed was filtered off, washed with water and air dried. The resulting 1,2,4-triazolo[4,3-a]pyridine 9 was dissolved in 7M methanolic ammonia (0.25 M with respect to 9) and was hydrogenated over Raney Nickel catalyst (0.5 equiv.) at 100 atm and 60 C over 48 hours. Once it reached room temperature, the mixture was filtered through a short plug of silica gel and concentrated in vacuo. Chromatography on silica gel using 05% MeOH in CH2Cl2 afforded analytically pure compounds 8a-e.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mishchuk, Alexander; Shtil, Natalia; Poberezhnyk, Mykola; Nazarenko, Konstiantyn; Savchenko, Timur; Tolmachev, Andrey; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 9; (2016); p. 1056 – 1059;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1461602-59-4, 3-(Methylamino)isonicotinic Acid, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 20. Synthesis of Compound 127 Methyl 3-(methylamino)pyridine-4-carboxylate To a stirred solution of 3-(methylamino)pyridine-4-carboxylic acid (11 g, 72.296 mmol, 1 equiv.) in MeOH (500 mL, 12349.455 mmol, 170.82 equiv.) was added SOCl2 (43.01 g, 361.478 mmol, 5 equiv.) dropwise at 0 C. The resulting mixture was stirred for 30 hours at 70 C. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 mL). The mixture basified to pH 8 with saturated NaHCO3 (aq.). The resulting mixture was extracted with EtOAc (2*20 mL). The combined organic layers were washed with brine (1*30 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure to afford methyl 3-(methylamino)pyridine-4-carboxylate (9 g, crude) as a yellow solid.

The synthetic route of 1461602-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goldfinch Bio, Inc.; Ledeboer, Mark W.; Daniels, Matthew H.; Yu, Maolin; Harmange, Jean-Christophe P.; US2020/102301; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem