Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate → Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-chloro-2-(3-fluorophenyl)-6-[(formylamino)methyl]nicotinate (2.6 g, 8.5 mmol) was stirred in phosphoryl chloride (80 mL) and heated at 90° C. for 1 hour. Evaporation and purification by flash column chromatography with ethyl acetate in hexanes (0-100%) gave the desired compound (0.60 g, 40%). LCMS calculated for C15H11ClFN2O2 (M+H)+: m/z=305.1. found: 304.9. 1H NMR (300 MHz, DMSO-d6): δ 8.26 (s, 1H), 7.91 (s, 1H), 7.60 (m, 1H), 7.43 (m, 3H), 7.38 (m, 1H), 3.60 (s, 3H).

Provenance & Evidence