1-Propanol → HCID 11632226, compound

Participants

Reaction Steps

Pyridine-3-boronic acid (0.39 g, 3.2 mmol) was added to 7-bromo-2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (1.0 g, 2.6 mmol) and 1-propanol (17 mL). The mixture was degassed and backfilled with nitrogen. Aqueous 2M sodium carbonate (1.6 mL), water (2 mL), triphenylphosphine (0.021 g, 0.079 mmol), and palladium (II) acetate (0.0058 g, 0.026 mmol) were added to the reaction mixture followed by subsequent degassing. The mixture became homogenous upon heating at reflux for 1 hour. After an additional 1 hour of heating, the reaction was cooled to ambient temperature and extracted into chloroform. The resulting solution was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (using a silica gel cartridge, eluting with CMA:chloroform ranging in ratios from 0:100 to 30:70) and concentrated under reduced pressure. The product was recrystallized from acetonitrile, filtered, and dried at 60° C. under vacuum to provide 0.66 g of 2-(ethoxymethyl)-1-(2-methylpropyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a white solid, mp 177-179° C.

Provenance & Evidence