7-Azaindole N-oxide 3-chlorobenzoate → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

POCl3 (10 mL) was added to 7-hydroxy-1H-pyrrolo[2,3-b]pyridin-7-ium 3-chlorobenzoate (1.0 g, 3.4 mmol). The resulting mixture was heated to 90° C. for 18 hours. The mixture was then cooled to room temperature and concentrated. The resulting residue was diluted with acetonitrile (“ACN”; 3 mL) and water (3 mL). The pH was adjusted with 50% NaOH to a pH of 9. The resulting solid was filtered and washed with water. The solid was then washed with DCM to give 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.30 g, 57% yield).

Provenance & Evidence