[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 44220114, compound

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Reaction Conditions

Reaction Steps

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (238 mg, 0.528 mmol) and (R)-2-(3-methyl-piperazin-1-yl)-quinoline (350 mg, 1.58 mmol) in anhydrous dimethylsulfoxide (6 mL) was heated at 50° C. overnight. The cooled reaction was diluted with saturated aqueous sodium bicarbonate (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography on silica gel (2/2/96 methanol/2 M ammonia in methanol/methylene chloride) afforded 110 mg (47%) of the title compound as an off-white solid: mp 78–82° C.; MS (ES) m/z441 [M+H]+; [α]D −33.0° (c 1.0, DMSO)

Provenance & Evidence