Sodium hydride → 2-ethoxymethyl-1-{2-[2-(phenylsulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline

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Reaction Steps

Solid sodium hydride (30 mg of 60% dispersion in mineral oil, 0.72 mmol) was added to a stirred solution of 1-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (2.15 g, 7.2 mmol) and phenyl vinyl sulfone (2.42 g, 14.4 mmol) in anhydrous tetrahydrofuran (29 mL). The reaction mixture was stirred at ambient temperature for about 1 hour, and then it was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide crude product as an oil. This material was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 0.95 g of 2-ethoxymethyl-1-{2-[2-(phenylsulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinoline as a colorless foam.

Provenance & Evidence