Ethanol → Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

Participants

Reaction Steps

A mixture of 2-chloro-3-cyanopyridine (330 g, 2.38 mol), ethyl 2-mercaptoacetate (361.2 g, 3.01 mol), sodium carbonate (265 g, 2.5 mol) and EtOH (1.2 l) was heated to reflux for 4.5 h. The reaction mixture was then cooled to ambient temperature and added to water (15 l). The resulting slurry was stirred for 0.5 h then filtered. The filter cake was washed with two portions of water (2×2.5 l). The solids were then dried to constant weight under vacuum at 45° C. to yield the title compound as a brown solid (493 g, 93%). δH (CDCl3) 8.68 (1H, dd, J 4.7, 1.2 Hz), 7.93 (1H, dd, J 8.5, 1.2 Hz), 7.29 (1H, dd, J 8.5, 4.7 Hz), 5.90 (2H, br), 4.38 (2H, q, J 7.0 Hz), 1.40 (3H, t, J 7.0 Hz). LCMS RT 2.9 minutes, 223 (M+H)+.

Provenance & Evidence