Sodium Chloride → 1-(4-amino-2-ethoxymethyl-7-[2-(1H-indol-3-yl)ethoxy]-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Participants

Reaction Steps

4-Amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (500 mg, 1.51 mmol), cesium carbonate (980 mg, 3.02 mmol), 3-(2-bromoethyl)indole (375 mg, 1.66 mmol), and DMF (10 mL) were combined and stirred at ambient temperature overnight followed by heating at 80° C. for 4 hours. The reaction mixture was cooled to ambient temperature and poured into 200 mL of water containing 20 g of sodium chloride. The resulting precipitate was filtered, dissolved in dichloromethane, and purified by flash column chromatography on silica gel, eluting with a gradient of 0-8% methanol in dichloromethane. Clean fractions were combined and concentrated. The solid was slurried in hot acetonitrile, filtered, and dried under reduced pressure to yield 305 mg of 1-(4-amino-2-ethoxymethyl-7-[2-(1H-indol-3-yl)ethoxy]-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as an off-white solid, mp 220.0-222.0° C.

Provenance & Evidence