Dimethylformamide → HCID 69585794, compound

Participants

Reaction Conditions

Reaction Steps

19.5 g (85.6 mmol) of 7-chloro-thieno[3,2-b]pyridine-2-carbothioic acid amide was added to 160 mL of a 1:1 DMF:THF solution mixture and cooled to 0° C. To this solution was slowly added 17.7 mL (128 mmol) of ethyl 2-chloroacetoacetate. After addition, the reaction was heated to 80° C. for sixteen hours. The reaction was cooled to room temperature and extracted with dichloromethane and water. The organic layer was separated and dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to afford 2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (15.6 g) in 54% yield. C14H11ClN2O2S2: APCI m/z 339.1/341.0 (pos.); 1H NMR (CDCl3): δ 8.68 (d, 1H , J=5.4 Hz), 8.24 (s, 1H), 7.51 (d, 1H, J=5.4 Hz), 4.36 (q, 2H, J=7.1 Hz), 2.77 (s, 3H), 1.38 (t, 3H, J=7.1 Hz) ppm.

Provenance & Evidence