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

Participants

Reaction Conditions

Reaction Steps

Add toluene (20 mL), (S)-2-sec-butylamino-6-chloro-isonicotinic acid methyl ester (2.01 g, 8.29 mmol), palladium acetate (186 mg, 0.83 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (516 mg, 0.83 mmol), cesium carbonate (5.40 g, 16.6 mmol), and sodium thiomethoxide (1.16 g, 16.6 mmol) to a sealed vessel flushed with nitrogen. Heat the sealed vessel at 90° C. overnight. Cool to room temperature and filter the solution through a filtering agent and concentrate the filtrate. Purify the residue (silica gel chromatography, eluting with ethyl acetate:hexanes 90:10) to give the title compound (1.4 g, 66%).

Provenance & Evidence