Imidazole → 8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide

Participants

Reaction Steps

To a mixture of 5-chloro-8-(4-hydroxypiperidin-1-yl)-N-methoxy-N-methylquinoline-7-carboxamide (372 mg, 1.06 mmol) and 1H-imidazole (0.362 g, 5.32 mmol) in N,N-dimethylformamide (2 mL) was added tert-butyldimethylsilyl chloride (0.240 g, 1.60 mmol). The reaction was stirred at room temperature overnight, then quenched with sat. sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 40% ethyl acetate in hexane, to give the desired product (0.312 g, 63%). LCMS calculated for C23H35ClN3O3Si (M+H)+: m/z=464.2; Found: 464.2.

Provenance & Evidence