Cesium carbonate → 1-[2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine (1.0 g, 2.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (70 mg, 0.068 mmol), cesium carbonate (1.25 g, 3.85 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.118 g, 0.204 mmol), pyrrolidin-2-one (0.25 mL, 3.3 mmol), and dioxane (2.75 mL) were added to a scintillation vial. The vial was sequentially flushed with nitrogen, sealed with a Teflon-lined cap, and heated at 110° C. for about 40 hours. After cooling to room temperature, the reaction mixture was diluted with chloroform and methanol and then filtered through CELITE filter aid. The filtrate was concentrated under reduced pressure to provide a tan solid. This material was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge and eluting with a gradient of 1-25% CMA in chloroform to provide 1-[2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]pyrrolidin-2-one.

Provenance & Evidence