Cesium carbonate → 2-Chloro-6-(methylpropylamino)-isonicotinic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Mix 2,6-dichloro-isonicotinic acid methyl ester (5 g, 24.2 mmol), methylpropyl-amine (3.2 g, 23.06 mmol), cesium carbonate (10 g, 31.2 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.5 g, 2.43 mmol), and palladium acetate (0.27 g, 1.21 mmol) in toluene (50 mL). Degas with argon, seal the vessel and heat at 80° C. for 16 h. Cool to room temperature and dilute with diethyl ether (50 mL). Filter through a filtering agent, concentrate, and purify (silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes to give the title compound as an oil (795 mg, 13.5%).

Provenance & Evidence