Tribromoborane-methyl sulfide → HCID 18186390, compound

Participants

Reaction Steps

To a solution of 1-({4-[6-(dimethylamino)(3-pyridyl)]phenyl}mehyl)-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.58 g, 1.07 mmol) in anhydrous dichloromethane (10 mL) under nitrogen at room temperature was added 1.0 M solution of boron tribromide-methyl sulfide complex in dichloromethane dropwise. After stirring for 5 hours, the reaction was quenched with ice-water and extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 30-50% ethyl acetate/hexane) to provide the title compound (0.346 g, 71% yield): 1H NMR (CDCl3) 8.42 (d, 1H), 7.69 (dd, 1H), 7.38 (m, 2H), 7.05 (d, 2H), 6.93 (m, 2H), 6.79 (m, 2H), 6.53-6.67 (m, 4H), 5.09 (br, 1H), 4.76 (t, 1H), 3.58 (m, 1H), 3.48 (m, 1H), 3.17 (m 1H), 3.13 (s, 6H), 2.92 (m, 2H), 2.07 (dt, 1H); ES-MS m/z 454 [M+H]+.

Provenance & Evidence