The origin of a common compound about 2-(2-Chloropyridin-3-yl)acetic acid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, and friends who are interested can also refer to it.

Reference of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. A new synthetic method of this compound is introduced below.

[0546] To a stirred solution of diisopropyl amine (1.65 mL, 1 1.7 mmol) in anthydrous THF (10 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 4.80 mL, 12.0 mmol) slowly between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooled to 0C. The solution of LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (1.00 g, 5.8 mmol) in anhydrous THF(20 mL) at 0C. Upon complete addition of the LDA solution the resultant bright yellow suspension was stirred at 0C for 15 minutes. A solution of (3-fluoro-4- isothiocyanatophenyl)(methyl)sulfane (1.63 g, 8.2 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture and heated to 65C for 1 8 hours. The reaction mixture was cooled to room temperature and the volatiles removed in vacuo. The resultant brown gum was redissolved in THF, cooled to 0C and 10% aq acetic acid 10 mL added slowly. Acetonitrile (5 mL) was added slowly until a yellow solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound as a yellow solid (546 mg, 20%). LC/MS: [M+l] 335. 1 HNMR (300 MHz, DMSO-d6): d 8.34 (d, J=8.1Hz, 1H), 7.85-8.20 (m, 1H), 7.61 (t, J = 8.6 Hz, 1H), 7.39-7.30 (m, 2H), 7.21 (d, J = 9.2 Hz, 1H), 2.52 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; TSAI, Kenneth, Y.; KINCAID, John; SARIN, Kavita, Yang; (319 pag.)WO2020/106303; (2020); A1;,
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