Tetrahydrofuran → HCID 68930143, compound

Participants

Reaction Steps

To a solution of N-methoxy-N-methyl-6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide (22.0 g, 59.7 mmol) in chloroform (20 mL) and THF (200 mL) in an ice bath was added dropwise a solution of methylmagnesium bromide (40 mL of a 3 M solution in diethyl ether, 120 mmol). After 1 hour another charge of methylmagnesium bromide (40 mL of a 3 M solution in diethyl ether, 120 mmol) was added, the reaction mixture stirred at room temperature for 1 more hour and then quenched by the addition of a 10% solution of hydrochloric acid (about 10 mL). The mixture was concentrated under reduced pressure, the residue taken up in dichloromethane (200 mL), and the solution washed successively with a saturated aqueous sodium bicarbonate solution and brine (100 mL each), dried over potassium carbonate, and filtered. The solution was concentrated under reduced pressure and chromatographed on silica gel (elution with 3% methanol in dichloromethane) to provide 7-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)heptan-2-one (12.6 g) as an oil that was used directly in the next step without further purification.

Provenance & Evidence