Water → 7-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-chloro-1H-pyrrolo[2,3-c]pyridine (3.00 g, 19.7 mmol) in THF (30 mL) cooled to 0° C. was added 60% NaH in mineral oil (0.940 g, 23.6 mmol NaH). The reaction mixture was stirred at 0° C. for 20 minutes. Iodomethane (6.20 g, 43.7 mmol) was added and the reaction mixture was stirred at 0° C. for 1 h and at 20° C. for 2 h. The mixture was poured into water (20 mL) and extracted with EtOAc (3×20 mL). The organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with a gradient of 17-33% EtOAc/petroleum ether to give the title compound as a yellow solid (2.8 g, 85%).

Provenance & Evidence