2,2'-Bipyridine → 8-Chloro-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (28.6 mg, 0.108 mmol), 2-bromo-3-chloro-5-(trifluoromethyl)pyridine (56.3 mg, 0.217 mmol), copper (I) iodide (20.6 mg, 0.108 mmol), 2,2′-bipyridyl (33.9 mg, 0.217 mmol) and cesium carbonate (70.7 mg, 0.217 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was stirred at 150° C. for 4 hrs. After cooling, the mixture was diluted with ethyl acetate, the precipitate was filtered through a pad of celite. The filtrate was extracted with ethyl acetate (×3). The combined organic layer was washed with 1N hydrochloric acid (×1) and brine (×1), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow amorphous (14.2 mg, 0.0320 mmol, 30%).

Provenance & Evidence