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248275-42-5

2-PYRIDIN-3-YL-THIAZOLE-5-CARBOXYLIC ACID synthesis

3synthesis methods
886370-75-8 Synthesis
Ethyl 2-pyridin-3-yl-thiazole-5-carboxylate

886370-75-8
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Yield:248275-42-5 80%

Reaction Conditions:

with lithium hydroxide monohydrate in tetrahydrofuran;water at 50; for 4 h;

Steps:

B. 2-(Pyridin-3-yl)thiazole-5-carboxylic acid

Lithium hydroxide monohydrate (0.770 g, 18.35 mmol) was added to a solution of ethyl 2-(pyridin-3-yl)thiazole-5-carboxylate (0.860 g, 3.67 mmol) in tetrahydrofuran (6 mL) and water (0.6 mL) and the reaction mixture was stirred in a heating block at 50 °C. After 4 hours, the mixture was cooled, poured into water and extracted with diethyl ether (1X). The aqueous layer was acidified by addition of 1 M hydrochloric acid (18.4 mL). The precipitated solids were collected by filtration, washed with water, and dried in a vacuum oven (50 °C / 28" Hg) to afford 2-(pyridin-3-yl)thiazole-5-carboxylic acid (0.603 g, 2.92 mmol, 80 % yield) as a tan solid. 1H NMR (400 MHz, CD3SOCD3) d 7.58 (dd, J = 8, 5 Hz, 1 H), 8.38 (dt, J = 8, 2 Hz, 1 H), 8.48 (s, 1 H), 8.73 (dd, J = 5, 2 Hz, 1 H), 9.20 (d, J = 2 Hz, 1 H), 13.76 (br s, 1 H); LC-MS (LC-ES) M+H = 207.

References:

WO2020/95215,2020,A1 Location in patent:Page/Page column 104-105