Acetic Acid → 5-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester (Preparation 4, 151 mg, 0.67 mmol) in ethanol (10 mL) was added sodium hydroxide (0.35 mL, 2M) and the stirred solution was heated to 70° C. for 2 h. The reaction mixture was allowed to cool to rt and left to stand for 16 h. The pH was adjusted to 4 by addition of glacial acetic acid, the solvents removed in vacuo to give a white solid, which was suspended in dichloromethane and filtered through a sinter, washing with additional dichloromethane. The filter cake was then washed with ethyl acetate (3×30 mL) and dried to give the title compound. δH (CD3OD): 6.97 (1H, s), 7.17 (1H, d), 7.83 (1H, d); m/z (ES+)=197 [M+H]+; RT=2.82 min.

Provenance & Evidence