1,4-Butanesultam → 2-sec-Butylamino-6-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-isonicotinic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Add 2-sec-butylamino-6-chloro-isonicotinic acid methyl ester (1.0 g, 4.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.189 g, 0.207 mmol), 2-(di-tert-butylphosphino)biphenyl (0.123 g, 0.413 mmol) and the sodium salt of [1,2]thiazinane 1,1-dioxide (0.844 g, 5.37 mmol) in toluene (10 mL) to a sealed flask flushed with nitrogen. Heat and stir the sealed flask at 100° C. for 18 h. Cool to room temperature and filter through a bed of filtering agent, and wash with dichloromethane. Concentrate the filtrate and purify (silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes) to give the title compound (0.533 g, 38%).

Provenance & Evidence