Sodium Carbonate → HCID 69507074, compound

Participants

Reaction Conditions

Reaction Steps

5-(7-Bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (2.5 g, 6.68 mmol) was dissolved in propanol (25 mL) and water (5 mL) and degassed with nitrogen for 5 minutes. Phenylboronic acid (1.97 g, 7.35 mmol), palladium (II) acetate (7 mg, 0.03 mmol), triphenylphosphine (0.17 g, 0.06 mmol), and sodium carbonate (0.85 g, 8.01 mmol) were added sequentially to the reaction mixture and heated at 100° C. overnight. The mixture was concentrated under reduced pressure and the residue was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure. Purification was performed with flash column chromatography on silica gel (eluting with 3% methanol in dichloromethane) to obtain 1.0 g of 5-(7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one.

Provenance & Evidence