[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 10001170, compound

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Reaction Conditions

Reaction Steps

To a stirred solution of 4-benzofuran-3-yl-butylamine (770 mg, 4.07 mmol) in 6 mL of anhydrous DMSO was added [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (611 mg mg, 1.36 mmol). The reaction mixture was heated to 50° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (3×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. Flash chromatography on SiO2 (5% MeOH/CH2Cl2) afforded 403 mg (74%) of the (S)-enantiomer of the title compound as a yellow oil. The fumarate salt was prepared, yielding 285 mg of a beige solid, m.p. 127-130° C.; MS (ESI) m/z 403 [M+H]+.

Provenance & Evidence