Water → HCID 86613464, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 41 mg, 1.04 mmol) was added to a stirred solution of 1-(4-chloro-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (prepared as described in U.S. Pat. No. 5,266,575 Comparative Example C1, 3.00 g, 10.4 mmol) and methyl vinyl sulfone (2.20 g, 20.7 mmol) in tetrahydrofuran (41 mL). The reaction mixture was stirred at room temperature for 17 hours. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an oil that was purified by flash chromatography (silica gel, eluted with ethyl acetate) to yield 1.8 g of 4-chloro-2-methyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a white solid.

Provenance & Evidence