Benzyl Bromide → HCID 59508044, compound

Participants

Reaction Steps

To a suspension of 2-(2-methoxy-pyridin-3-yl)-3-piperidin-4-yl-1H-indole (0.13 g, 0.42 mmol) in dichloromethane (5 ml) was added diisopropylethylamine (0.22 ml, 1.25 mmol) followed by the benzyl bromide (0.075 g, 0.44 mmol). The reaction was stirred at room temperature for 2 h followed by addition of ethyl acetate and water. The organic layer was separated and washed with water, dried using Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography (SiO2, 100% EtOAc). The desired product was obtained as a yellow solid (0.080 g, 48%). M.p.=97-101° C.; 400 M Hz 1H NMR (DMSO-d6) 10.99 (s, 1H), 8.24 (dd, J1=7.2 Hz, J2=2.0 Hz, 1H), 7.70 (m, 2H), 7.34-7.24 (m, 6H), 7.13 (dd, J1=7.6 Hz, J2=5.2 Hz, 1H), 7.07 (m, 1H0, 6.98 (m, 1H), 3.86 (s, 3H), 3.48 (s, 2H), 2.92 (m, 2H), 2.56 (m, 1H), 2.15 (m, 2H), 1.93 (m, 2H), 1.64 (m, 2H); LCMS: 398.76 (M+1).

Provenance & Evidence