Pyridine-derivatives

Synthetic Route of 1033610-45-5, 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. 1033610-45-5, name is 4-Bromo-3,5-dimethoxypyridine. A new synthetic method of this compound is introduced below.

To an ice-cooled suspension of sodium hydride (60% dispersion in mineral oil, 650 mg, 16.3 mmol) in dry DMF (10 ml) was added 4-methoxybenzyl alcohol (2.24 g, 16.3 mmol) drop-wise via syringe. Vigorous evolution of hydrogen was observed and the reaction was allowed to warm to room temperature and stirred for 15 minutes. 4-Bromo-3,5-dimethoxypyridine (1.17 g, 5.41 mmol) was added and the reaction heated to 900C overnight. After cooling, only trace starting material could be detected by TLC analysis and the reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water 3 times then brine, dried over MgSO4 and concentrated onto silica-gel under reduced pressure. The solid residue was purified by flash chromatography (silica-gel, eluted sequentially with EtOAc : hexanes, 2:1, 1:0) to give the product as a tan solid (865 mg, 58%). 1H-NMR (300 MHz, CDCl3) delta 7.96 (s, 2H), 7.33 (d, J= 8.5 Hz, 2H), 6.84 (d, J= 8.5 Hz, 2H), 5.11 (s, 2H), 3.89 (s, 6H), 3.78 (s, 3H). MS (ES+) m/z 276.1 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033610-45-5, 4-Bromo-3,5-dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BIONOMICS LIMITED; WO2008/70908; (2008); A1;,
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, SDS of cas: 139585-48-1, blongs to pyridine-derivatives compound. SDS of cas: 139585-48-1

To a mixture of 2-chloro-5-methoxy-pyridine (6.0 g, 42 mmol) in THF (50 mL) was added lithium diisopropylamide (2.0 M in THF, 42 mL, 83.6 mmol) dropwise at -78 C. The reaction mixture was stirred at -78 C for 1 hour. A.A-di methyl formamide (5.0 mL, 83.6 mmol) was added to the reaction mixture at -78 C, and the mixture was stirred for 1 hour. Saturated NH4Cl solution (100 mL) was added to the reaction mixture. The solution was extracted with EtOAc (200 mL c 2). The combined organic layers were dried over anhydrous Na^SCL and concentrated. The residue was purified by column chromatography on silica gel (0- 25 % EtOAc in petroleum ether) to afford the title compound (5.5 g, 77 %) as a white solid. ‘H NMR (400 MHz, CDCl3) d 10.41 (s, 1H), 8.27 (s, 1H), 7.59 (s, 1H), 4.03 (s, 3H).

The synthetic route of 139585-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1083197-78-7, 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. 1083197-78-7, name is 4-(Trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

4-(trifluoromethyl)nicotinaldehyde was added to a solution of l,2-diamino-4,5- difluoropyridinium 2,4,6-trimethylbenzenesulfonate (47-4; 0.2 g, 0.000579 mol) in ethanol (20 mL) while stirring, followed by the addition of l,8-diazabicyclo[5.4.0]undec- 7-ene. The reaction mixture was stirred for 12 h at RT. It was then concentrated under vacuum, diluted with water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The collected organic parts were concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compounds. 1H NMR (400 MHz, DMSO) delta 8.20 (s, 1 H), 9.09-9.06 (m, 1 H), 9.03-9.02 (d, J = 4 Hz, 1 H), 7.99-7.77 (d, J = 8 Hz, 1 H), 7.61-7.55 (m, 1 H). HPLC purity- 99.13%, MS (M+1): 301.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1083197-78-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, D. Jonathan; CAI, Jaiqiang; CARSWELL, Emma; COOKE, Andrew; HOYT, Scott, B.; LONDON, Clare; MACLEAN, John; RATCLIFFE, Paul; TAYLOR, Jerry Andrew; XIONG, Yusheng; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2013/43520; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89510-90-7 , The common heterocyclic compound, 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine, molecular formula is C5H4ClFN2, 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 solution of 2-chloro-5-fluoropyridin-4-amine (900mg, 6.41 mmol, 1 eq) in Morpholine (9ml_) was irradiated under microwave at 180C for 90min in 30ml_ vial. TLC analysis indicated formation of polar spot. Then, the reaction mixture was cooled to RT and poured on ice-waterto give a off white precipitate; which was purified by column chromatography (Silica gel 100-200mesh) using 40% EtOAc in petroleum ether as an eluent to give 5-fluoro-2- morpholinopyridin-4-amine (720mg, 57.14% yield) as an off-white solid. LC- MS: m/z 198.0 (M+ H).

The synthetic route of 89510-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; PRAKESCH, Michael; JOSEPH, Babu; MORIN, Justin-Alexander; (441 pag.)WO2019/153080; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1070892-04-4, 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 1070892-04-4, name is 5-Bromo-2-(trifluoromethyl)isonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-[5-Chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1- sulfonyl)-4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenoxy]-butan-1 -ol (270.0 mg, 0.49 mmol), S-bromo^-trifluoromethyl-isonicotinonitrile (112 mg, 0.45 mmol), Pd(Ph3P)4 (57 mg, 0.05 mmol) and Na2CO3 (286 mg, 2.7 mmol) in dioxane (4 ml_) and water (0.4 ml_) was degassed with N2 for 5 min. The reaction vessel was sealed and then heated at 100 0C for 16 hrs. The mixture was then partitioned between ethyl acetate (20 mL) and water (10 ml_). The organic layer was washed with brine (2 x 10 ml_), dried over MgSO4, filtered and concentrated to give a material which was purified by TLC plates eluting with 30% acetone in hexanes to give 5-[2-chloro-5-(4,4-dimethyl- 3,4-dihydro-2H-quinoline-1-sulfonyl)-4-(4-hydroxy-butoxy)-phenyl]-2-trifluoromethyl- isonicotinonitrile 11-1 as a white solid (95 mg). MS: 594.2 (M+H)+; tR = 2.94 min (method 1).

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 1070892-04-4, 5-Bromo-2-(trifluoromethyl)isonicotinonitrile.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 132521-70-1, 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.132521-70-1, name is 6-(4-Methylpiperazin-1-yl)nicotinic acid, molecular formula is C11H15N3O2, molecular weight is 221.26, as common compound, the synthetic route is as follows.

To a solution of 6-(4-(tert-butoxycarbonyl) piperazin-1-yl) nicotinic acid (123.7 mg, 0.40 mmol) and tertbutyl 2-amino-4-(pyridin-3-yl) phenylcarbamate (1, 3, 2-di- oxaborolane) (114.5 mg, 0.40 mmol) in Py (2.5 ml) was added EDCI (230 mg, 1.20 mmol). The mixture was stirred at room temperature for overnight. The residue was purified by preparative TLC (silica gel, GF254 10-40 u, 25×25 cm) with PE/EA (2:1) to afford a yellow solid (165 mg, 72%).

Statistics shows that 132521-70-1 is playing an increasingly important role. we look forward to future research findings about 6-(4-Methylpiperazin-1-yl)nicotinic acid.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1254473-66-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1254473-66-9 as follows.

Acetyl chloride (41.99g, 534.88mmol) was added dropwise to a solution of 1E 1-(3,5-dichloropyridine-4-)ethanol(85.60g, 445.74mol), triethylamine (90.21g, 891.47mmol) in dichloromethane (1.5L) at 20C, and the mixture was stirredat 20C for 1 hour. When TLC showed the completion of the reaction, the solvent was evaporated under reduced pressureand the residue was purified by column chromatography to give the title compound (as a colorless oil, 57.10g, yield54.7%). 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.44 (s, 2H), 6.25 (q, J=6.8 Hz, 1H), 2.09 (s, 3H), 1.63 (d, J=7.2Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1254473-66-9, its application will become more common.

Reference:
Patent; Harbin Zhenbao Pharmaceutical Co., Ltd.; Medshine Discovery Inc.; CHEN, Shuhui; CHEN, Zhengxia; DAI, Meibi; XIE, Cheng; LI, Peng; ZHANG, Yang; LIANG, Guibai; WANG, Qiang; LIAO, Jiangpeng; SUN, Fei; HU, Guoping; LI, Jian; (166 pag.)EP3333157; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59290-81-2, 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid. A new synthetic method of this compound is introduced below.

Example 6a 2-methyl-5-nitro-N-phenylnicotinamide To a solution of 2-methyl-5-nitronicotinic acid (364 mg, 2 mmol), aniline (186 mg, 2 mmol) and DIEA (774 mg, 6 mmol) in DMF (6 mL) is added HATU (798 mg, 2.1 mmol). The reaction mixture is stirred at room temperature for 2 hours. The solvent is removed by rotary evaporation and the crude product is purified by silica gel flash chromatography, eluted with 40% ethyl acetate in hexane to afford-methyl-5-nitro-N-phenylnicotinamide as a light green solid. MS m/z 258.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59290-81-2, its application will become more common.

Reference:
Patent; Novartis AG; Cheng, Dai; Han, Dong; Zhang, Guobao; Wan, Yongqin; Xie, Yun Feng; Jiang, Jiqing; Gao, Wenqi; Pan, Shifeng; US9216964; (2015); B2;,
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 117873-72-0, name is 2,6-Dibromo-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,6-Dibromo-4-methoxypyridine

(1) 3-(trifluoromethyl) phenol (3.34 g; 0.0187*1.1 mol) was dissolved in dimethyl formamide (about 30 ml). Further, sodium hydride [0.78 g (ca. 60% in mineral oil), 0.0187*1.0 mol] and then 2,6-dibromo-4-methoxy pyridine (5.00 g, 0.0187 mol) were added to the solution. The obtained solution was stirred at about 120 C. for about 2 hours and, thereafter, allowed so as to stand and cooled to room temperature. The obtained reaction solution was distributed in hexane-saturated sodium bicarbonate water. The organic phase separated from the reaction solution was washed with saturated brine, and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane), and the obtained purified product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield weight: 3.23 g; yield percentage: 50%; solid; melting point: 57 to 60 C.; 1 H-NMR (60 MHz, CDCl3, delta): 3.75(3H, s), 6.26(1H, d, J=2 Hz), 6.75(1H, d, J=2 Hz), 7.0-7.6(4H, complex).

With the rapid development of chemical substances, we look forward to future research findings about 117873-72-0.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6159901; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19235-89-3, Adding some certain compound to certain chemical reactions, such as: 19235-89-3, name is 4-Chloropyridine-2-carbonitrile,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 19235-89-3.

To a stirred solution of cyclohexanol (2.84 g, 3.00 mL, 2.84 mmol) in 1-methyl-2-pyrrolidinone (20 mL) was added sodium hydride (1.19 g of 60% dispersion, 29.8 mmol) in small portions over 5 minutes. After stirring for an additional 5 minutes, 2-chloro-4-cyanopyridine (3.75 g, 27.0 mmol) was added and the resulting red-brown solution was heated at 100 C. for 10 minutes. The reaction mixture then was poured onto ice. The mixture was diluted with water and extracted with ether. The combined organic phases were washed with water and brine, dried (magnesium sulfate) and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 4.17 g (76%) of the desired product as a cloudy oil which solidified on standing: 1H NMR (CDCl3) delta 8.44 (d, J=5.8 Hz, 1H), 7.17 (d, J=2.4 Hz, 1H), 6.95 (dd, J=2.4, 5.8 Hz, 1H), 4.40-4.33 (m, 1H), 1.98-1.95 (m, 2H), 1.82-1.79 (m, 2H), 1.60-1.52 (m, 3H), 1.45-1.32 (m, 3H) ppm. 13C NMR (CDCl3) delta 164.3, 152.2, 135.0, 117.3, 116.4, 113.9, 76.4, 31.1, 25.2, 23.4 ppm.

According to the analysis of related databases, 19235-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genzyme Corporation; US2005/176761; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem