Synthetic Route of 17874-79-2, Adding some certain compound to certain chemical reactions, such as: 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid,molecular formula is C8H7NO4, 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 17874-79-2.
[00455] To a solution of 5-methoxycarbonylpyridine-2-carboxylic acid (0.5 g, 2.76 mmol) in DCM (10 mL) was added (COCl2)2 (1.7 g, 13.8 mmol) and a drop of DMF at 0C, the resulting mixture was stirred at room temperature (approximately 25 C) for 1 hour, at which point TLC showed the reaction was over. The reaction mixture was concentrated to give methyl 6-chlorocarbonylpyridine-3-carboxylate. To a solution of EtMgBr (2.76 mL, 1 M in THF, 2.76 mmol) was added a solution of indol (315 mg, 2.7 mmol) in ether (anhydrous, 10 mL). The resulting two-phase system was allowed to stand for 15 min under stirring whereupon ZnCl2 (370 mg, 2.7 mmol) was added with stirring. The two-phase system was allowed to stand for 30 min when compound methyl 6- chlorocarbonylpyridine-3-carboxylate (560 mg, 2.76 mmol) in anhydrous ether (5 ml) was added. The reaction mixture was stirred at room temperature (approximately 25 C) for 2 hours, whereupon NFLC1 (15 ml) was added. The reaction mixture was diluted with water, extracted with DCM, dried over Na2S04, concentrated and purified by SGC (PE: EA=l5:l) to give the title compound, yield 24%, as a yellow syrup. 1H NMR (300 MHz, DMSO-de) 4.03 (s, 3H), 6.66 (d, J = 4.0 Hz, 1H), 7.31-7.42 (m, 2H), 7.60 (d, / = 7.6 Hz, 1H), 7.92 (d, / = 3.6 Hz, 1H), 8.16 (d, J = 8.0 Hz, 1H), 8.52-8.54 (m, 2H), 9.32 (s, 1H), MS (ESI+): m/z calc for[CieH NiOs] 280.08, Found: 281.6[M+H]+.
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Reference:
Patent; BETH ISRAEL DEACONESS MEDICAL CENTER, INC.; CHAIKOF, Elliot; SUN, Lijun; (224 pag.)WO2019/195682; (2019); A1;,
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