Cesium carbonate → 2-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxopyrrolidin-1-yl]-3-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-4-iodo-3-methylbenzonitrile (1.29 g), (4S,5S)-4-hydroxy-4,5-dimethylpyrrolidin-2-one (500 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (343 mg), tris(dibenzylideneacetone)dipalladium(0) (177 mg) and cesium carbonate (1.86 g) in 1,4-dioxane (4 mL) was tightly sealed, and the mixture was stirred at 120° C. for 3 hr using microwave reactor. The reaction mixture was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=30→70%, basic silica gel eluent:ethyl acetate/hexane=30→80%), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound as colorless crystals (yield: 603 mg, 56%).

Provenance & Evidence