[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 44220113, compound

Participants

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 (0.165 g, 0.367 mmol) and (S)-2-(3-methyl-piperazin-1-yl)-quinoline (250 mg, 1.10 mmol) in anhydrous dimethylsulfoxide (4 mL) was heated at 50° C. overnight. The cooled reaction was diluted with saturated aqueous sodium bicarbonate (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (30 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 100 mg (62%) of the title compound as an off-white solid: mp 141–144° C.; MS (ES) m/z 441 [M+H]+; [α]D −36.5° (c 1.0, DMSO).

Provenance & Evidence