Cesium carbonate → (S)-2-sec-Butylamino-6-(2-oxopropyl)-isonicotinic acid methyl ester

Participants

Reaction Steps

Dissolve 2-chloro-6-(2-oxopropyl)-isonicotinic acid methyl ester (200 mg, 0.88 mmol), palladium (II) acetate (2.0 mg, 0.009 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (8.2 mg, 0.014 mmol) and cesium carbonate (458 mg, 1.23 mmol) in toluene (2 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (0.105 mL, 1.0 mmol) to the solution under nitrogen and heat the sealed mixture overnight at 100° C. Cool the reaction to room temperature. Dilute with diethyl ether and filter through a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, 0:100 to 20:80 ethyl acetate:hexanes) to give the title compound (22%).

Provenance & Evidence