Hydrochloric Acid → 8-((cis)-4-Fluoropyrrolidin-3-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline hydrochloride salt

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Reaction Steps

Crude (cis)-benzyl 3-fluoro-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate (1.0 g, 2.0 mmol) and palladium on carbon (1 g, 50% on a molar basis) were added to a mixture of ethanol and 1% HCl (v/v) and placed under hydrogen in a balloon with vigorous stirring. After 18 hours, the crude mixture was passed through Celite, rinsed several times with ethanol, and the collected filtrate was evaporated. The crude material was purified on silica gel using a 6% solution of ammonium hydroxide in methanol and dichloromethane to yield free base product, which, when subjected to HCl in dichloromethane and subsequent precipitation in diethyl ether yielded 150 mg (16% isolated yield) of highly pure product. MS APCI (+) m/z 423.3 (M+1) detected.

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