Methanol → Methyl 1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Participants

Reaction Steps

Add to a 0° C. solution of 1H-pyrrolo[3,2-c]pyridine-2-carboxaldehyde (9b-1, 3.24 g, 22.19 mmol) in methanol under argon, sodium cyanide (5.44 g, 111 mmol) and manganese dioxide (9.65 g, 111 mmol). Stir the reaction mixture for 5 h, filter through Celite® and dilute with 500 ml EtOAc. Wash the organic layer with water (2×) and brine, dry over sodium carbonate, filter, and concentrate to provide the title compound (3.27 g) as a pure tan solid. Prepare 1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid amide 6b-1 from 5b-1 by any of the above described procedures for the synthesis compound 6a-1 from ethyl ester 4a-1.

Provenance & Evidence