2,2'-Bipyridine → 8-Chloro-5-(1-ethylpropyl)-1-(3-methyl-5-nitropyridin-2-yl)-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 (30.6 mg, 0.116 mmol), 2-bromo-3-methyl-5-nitropyridine (50.4 mg, 0.232 mmol), copper(I) iodide (22.1 mg, 0.116 mmol), 2,2′-bipyridyl (36.2 mg, 0.232 mmol) and cesium carbonate (75.6 mg, 0.232 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was stirred at 150° C. for 5 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 0-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow amorphous (13.5 mg, 0.0338 mmol, 29%).

Provenance & Evidence