Water → Dicyclopropyl[1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate (90 mg, 0.239 mmol) in tetrahydrofuran (2.4 mL) was added a solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.0 M, 1.4 mL, 1.4 mmol) at room temperature. The mixture was stirred at 60° C. for 1.5 hr. Water was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 25-60% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/diisopropyl ether to give the title compound (40.2 mg, 0.094 mmol, 39%) as colorless crystals.

Provenance & Evidence