Thiophenol → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(2,4-difluorophenyl)methyl]-3-[(phenylthio)methyl]-,methyl ester

Participants

Reaction Steps

To a stirring solution of methyl 1-(2,4-difluorobenzyl)-3-[(dimethylamino)methyl]-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.906 g, 2.52 mmol) in DCM (20 mL) was added ethyl chloroformate (0.240 mL, 2.52 mmol). The pale yellow homogeneous solution was stirred for 20 minutes. To this stirring solution was added a solution of benzenethiol (0.416 g, 3.78 mmol) and diisopropyl ethylamine (0.814 g, 6.3 mmol) in DMF (10 mL). The reaction was stirred for 16 hours at ambient temperature. The reaction was concentrated in vacuo and purified by flash chromatography yielding a white powder (0.405 g, 40%). 1H NMR (400 MHz, CDCl3) δ ppm 4.01 (s, 3H) 4.27 (s, 2H) 5.32 (s, 2H) 6.74-6.80 (m, 1H) 6.81-6.90 (m, 2H) 7.12 (s, 1H) 7.17-7.24 (m, 3H) 7.26-7.29 (m, 2H) 8.50 (s, 1H) 8.78 (s, 1H). LCMS (APCI, M+H): 425.1.

Provenance & Evidence