Category: pyridine-derivatives

Application of 136888-20-5, 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. 136888-20-5, name is 5-Fluoro-3-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

A suspension of S-fluoro-3-nitropyridin-2-ol (500 mg, 3.16 mmol) and cesiumcarbonate (2061 mg, 6.33 mmol) in DMF (8 mL) was stirred at rt for 10 mm, and 1-bromo-2-fluoroethane (723 mg, 5.69 mmol) was then added. The mixture was stirred at75 C for 4 h. Two products with the desired MS were detected. The mixture was dilutedwith ethyl acetate (15 mL) and filtered through Celite. The filtrate was concentratedunder vacuum to dryness. The residue was dissolved in ethyl acetate (100 mL), washedwith water (20 mL) and brine (20 mL), and dried over anhydrous Mg504. The desired product, 5 -fluoro- 1 -(2-fluoroethyl)-3 -nitropyridin-2( 1 H)-one (146 mg, 0.715 mmol, 22.61 % yield), was isolated as a yellow solid by ISCO (40 g solica gel, 30-50% ethyl acetate/hexane).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136888-20-5, 5-Fluoro-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
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. 102830-75-1, name is 3-Bromo-5-chloro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 102830-75-1

To a solution of 3-bromo-5-chloro-2-methoxypyridine (5.00 g, 33.7 mmol) in toluene (100 mL) was added tert-butyl 3-aminoazetidine-1-carboxylate (5.8 g, 18.5 mmol), Xantphos (650 mg, 1.12 mmol), Cs2CO3 (14.6 g, 44.9 mmol) and Pd2(dba)3 (514 mg, 0.562 mmol). The reaction mixture was stirred at 60 C. under nitrogen for 4 days. After cooling to RT, the reaction mixture was filtered, washed with ethyl acetate (100 mL), the organic layer washed with water (60 mL), brine (60 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/hexane) to obtain 5.6 g of tert-butyl 3-((5-chloro-2-methoxypyridin-3-yl)amino)azetidine-1-carboxylate as a white-yellow oil (80%): 1H NMR (400 MHz, CDCl3) delta 7.39 (d, J=2.2 Hz, 1H), 6.36 (d, J=2.2 Hz, 1H), 4.52 (d, J=6.5 Hz, 1H), 4.24 (dd, J=8.9, 7.1 Hz, 2H), 4.05 (m, 1H), 3.89 (s, 3H), 3.70 (dd, J=9.1, 4.8 Hz, 2H), 1.37 (s, 9H); MS (ES) m/z 314 (M+H).

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, 102830-75-1, 3-Bromo-5-chloro-2-methoxypyridine.

Reference:
Patent; Jacobsen, Eric Jon; Blinn, James Robert; US2015/210671; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 407-22-7, 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 407-22-7, name is 2-Fluoro-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Add NBS (35.6 g, 0.20 mole) to a solution of 6-fluoro-2-methylpyridine (20 mL, 0.19 mole) in EtOAc (400 mL) at room temperature. When the temperature reaches 45 C., add AIBN (400 mg, 2.4 mmol). Heat the mixture at 65 C. for 6 h, then cool to room temperature and add hexane (1 L). Remove the white precipitate by filtration and wash the solid with hexane/EtOAc (1:1). Wash the filtrate with small amounts of aqueous Na2S2O3, NaHCO3, and brine. Dry the organics (Na2SO4), filter, then remove most of the solvent under vacuum at room temperature. Transfer the remaining solution to a distillation set-up. Remove the remaining solvent by distilling at atmospheric pressure, followed by the unreacted starting material at 80 mm (bp ca 70 C.; 11.2 g) and then the title product at 1 mm (bp ca 75 C.; 12.1 g, 32%). NMR (300 MHz; CDCl3): 7.82 (1H; dd); 7.35 (1H; dd); 6.90 (1H; dd); 4.50 (2H; s).

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 407-22-7, 2-Fluoro-6-methylpyridine.

Reference:
Patent; Gavardinas, Konstantinos; Green, Jonathan Edward; Jadhav, Prabhakar Kondaji; Matthews, Donald Paul; US2010/69404; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 944401-77-8, 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. 944401-77-8, name is 2-Amino-4-fluoropyridine. A new synthetic method of this compound is introduced below.

0294] Solid NBS (78 mg, 0.43 mmol) was added to a solution of 3-fluoropyridin-2-amine HCl salt (162 mg, 0.72 mmol) in ACN (4 mL) at RT with stirring. The reaction was shielded from light and stirred under nitrogen. After 1.5 h, an additional amount of NBS (15 mg, 0.084 mmol) was added to the reaction. Checking the reaction again after 1.5 h, an additional amount of NBS (15 mg, 0.084 mmol) was added to the reaction until the starting material had been consumed by LCMS. After 1 h7 the solvent was removed under reduced pressure and the residue purified by silica flash chromatography eluting with 50% ethyl acetate/hexane to afford 5-bromo-4-fluoropyridin-2-amine as a ivory solid (92 mg, 68%). LC/MS (m/z): 190.9/192.9 (MH+), Rt 1.02 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,944401-77-8, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2176-62-7, Perchloropyridine, 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: Perchloropyridine, blongs to pyridine-derivatives compound. name: Perchloropyridine

In a 1000 mL three-necked flask, add 600 mL of DMI and anhydrous KF146.72 g with a purity of 99% and a particle size of 20-50 um. Stirring and distilling under reduced pressure (130-135 C / 60 mmHg)60 g solvent with water evaporation, the measured water content of less than 1000 ppm, heated to 90 C, adding purity of 97% of the five chloropyridine 129.40 g, After 1.5 h of incubation, heating was stopped, the reaction mixture was cooled and the reaction mixture was filtered to obtain filtrate and residue. The residue was washed with 100 mL of DMI and suction filtered to obtain a washing solution. Combined washing liquid and filtrate, distillation, collecting 65 ~ 70 , 5 KPa fractions, namely 3,5-dichloro-2,4,6-trifluoropyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2176-62-7, Perchloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan Fusida Biotechnology Development Co., Ltd; Luo, Qian; Peng, Zhou; Li, Zhou; Wang, Lei; Zhang, Hua; Pi, Yawei; (8 pag.)CN106008331; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1121-60-4, 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.1121-60-4, name is Picolinaldehyde, molecular formula is C6H5NO, molecular weight is 107.11, as common compound, the synthetic route is as follows.

General procedure: Equimolar mixture of pyridine carboxaldehyde deriva-tives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by the addi-tion of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice, precipitates were formed which were collected by filtration to afford compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals.

The chemical industry reduces the impact on the environment during synthesis 1121-60-4, I believe this compound will play a more active role in future production and life.

Reference:
Article; Khan, Momin; Ahmad, Riaz; Rehman, Gauhar; Gul, Naeem; Shah, Sana; Salar, Uzma; Perveen, Shahnaz; Khan, Khalid Mohammed; Letters in drug design and discovery; vol. 16; 9; (2019); p. 984 – 993;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1101120-05-1, 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 1101120-05-1 as follows.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1101120-05-1, its application will become more common.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 81719-53-1, 3,5-Dichloropyridine-2-carboxylic 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, name: 3,5-Dichloropyridine-2-carboxylic Acid, blongs to pyridine-derivatives compound. name: 3,5-Dichloropyridine-2-carboxylic Acid

Production Example 32 (1) [0773] 5.53 ml of thionyl chloride was added to a mixture of 4.7 g of 3,5-dichloropicolinic acid, 49 ml of toluene and 0.1 ml of DMF, and the mixture was stirred at 80C for 2 hours. The cooled reaction mixture was concentrated under reduced pressure, and 49 ml of toluene, 4.84 g of N-methyl-4-trifluoromethylsulfanylaniline and 8.05 ml of diisopropylethylamine were added, and the mixture was stirred at 80C for 2 hours. The cooled reaction mixture was poured to a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 8.92 g of 3,5-dichloro-N-methyl-N-(4-trifluoromethylsulfanylphenyl)pi colinamide. RRN 1573,5-Dichloro-N-methyl-N-(4-trifluoromethylsulfanylphenyl)pi colinamide [0774] 1H-NMR(CDCl3)delta: 8.28(1H, d), 7.58(1H, d), 7.50(2H, d), 7.19(2H, d), 3.54(3H, s).

The synthetic route of 81719-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; MAEHATA, Ryota; MIZUNO, Hajime; SHIMIZU, Chie; NOKURA, Yoshihiko; EP2881386; (2015); A1;,
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. 65169-43-9, name is Methyl 2-chloro-5-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 65169-43-9

j0352] To a sealed tube containing methyl 2-chloro-5-me- thylnicotinate (CAS 65 169-43-9) (745 g, 4.01 mmol), Cul (38 mg, 0.2 mmol), LiC1 (169 g, 4.01 mmol), and Pd(PPh3)4 (231 g, 0.2 mmol) in toluene (15 mE) was added 2-(tributyl- stannyl)pyrimidine (1.5 mE, 4.4 mmol), and the reaction mixture was heated at 120 C. overnight. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried over Mg504, filtered and evaporated. Purification via silica gel chromatography (0-50% EtOAc in hexanes) gave the title compound (494 g, 52%). MS (ESI) mass calcd. for C,2H,,N302, 229.1; mlz found 229.99.

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, 65169-43-9, Methyl 2-chloro-5-methylnicotinate.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 102830-75-1, 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. 102830-75-1, name is 3-Bromo-5-chloro-2-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-5-chloro-2-methoxypyridine (5.00 g, 33.7 mmol) in toluene (100 mL) was added tert-butyl 3-aminoazetidine-1-carboxylate (5.8 g, 18.5 mmol), Xantphos (650 mg, 1.12 mmol), Cs2CO3 (14.6 g, 44.9 mmol) and Pd2(dba)3 (514 mg, 0.562 mmol). The reaction mixture was stirred at 60 C. under nitrogen for 4 days. After cooling to RT, the reaction mixture was filtered, washed with ethyl acetate (100 mL), the organic layer washed with water (60 mL), brine (60 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/hexane) to obtain 5.6 g of tert-butyl 3-((5-chloro-2-methoxypyridin-3-yl)amino)azetidine-1-carboxylate as a white-yellow oil (80%): 1H NMR (400 MHz, CDCl3) delta 7.39 (d, J=2.2 Hz, 1H), 6.36 (d, J=2.2 Hz, 1H), 4.52 (d, J=6.5 Hz, 1H), 4.24 (dd, J=8.9, 7.1 Hz, 2H), 4.05 (m, 1H), 3.89 (s, 3H), 3.70 (dd, J=9.1, 4.8 Hz, 2H), 1.37 (s, 9H); MS (ES) m/z 314 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102830-75-1, 3-Bromo-5-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Confluence Life Sciences, Inc.; Jacobsen, Eric Jon; Blinn, James Robert; US9145393; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem