Dimethylformamide → Methyl 2-(3-((4-(difluoromethyl)phenyl)difluoromethyl)-2-oxoimidazolidin-1-yl)isonicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-oxoimidazolidin-1-yl)isonicotinate (0.50 g, 2.26 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (0.10 g, 60% dispersion in mineral oil, 2.5 mmol) at 0° C. The resulting solution was stirred at 0° C. for 30 minutes, followed by the addition of 1-(bromodifluoromethyl)-4-(difluoromethyl)benzene (0.58 g, 2.26 mmol). The mixture was warmed to ambient temperature and stirred for 55 hours. 1-(Bromodifluoromethyl)-4-(difluoromethyl)benzene (0.13 g, 0.5 mmol) was again added and the reaction was stirred at 60° C. for 5 hours then concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with hexanes and ethyl acetate (from 10:1 to 1:1) to give methyl 2-(3-((4-(difluoromethyl)phenyl)-difluoromethyl)-2-oxoimidazolidin-1-yl)isonicotinate as a colorless solid (0.09 g, 13%): MS (ES+) m/z 397.8 (M+1).

Provenance & Evidence