Phosphorus oxychloride → Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

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Reaction Steps

A suspension of methyl 1-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (47.4 g) in phosphorus oxychloride (64.4 ml) was heated to reflux and stirred for 50 minutes then allowed to cool. The phosphorus oxychloride was removed in vacuo and the residue partitioned between dichloromethane (600 ml) and saturated sodium carbonate (600 ml). The aqueous layer was separated and further extracted with dichloromethane (600 ml). The organic layers were combined, dried (MgSO4) and the solvent removed. The residue was purified by column chromatography on a Biotage silica column (800 g) eluting with dichloromethane to yield the title compound as a white solid (42.7 g).

Provenance & Evidence