Phosphorus oxychloride → Methyl 8-chloroimidazo[1,5-a]pyridine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-2-formylaminomethyl-isonicotinic acid methyl ester (1.5 g, 6.6 mmol) and phosphorous oxychloride (1.3 mL, 14.2 mmol) in toluene (80 mL) was stirred at 90° C. for 15 minutes, then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The organic layer was separated and washed with water and brine, dried (Na2SO4), filtered and concentrated to give the title compound as a pale yellow solid (1.3 g, 93%). LCMS (method B): RT=2.38 min, [M+H]+=211.

Provenance & Evidence