[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 10387289, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(7-methoxy-benzofuran-3-yl)-propylamine (770 mg, 3.75 mmol) in 5 mL of anhydrous DMSO was added [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (563 mg, 1.25 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 120 mg (23%) of the (S)-enantiomer of the title compound as a yellow oil. The fumarate salt was prepared, yielding 132 mg of a beige solid, m.p. 155-160° C.; MS (ESI) m/z 419 [M+H]+.

Provenance & Evidence