2-Bromopropane → 1H-Indole,4-bromo-1-(1-methylethyl)-6-(trifluoromethyl)-

Participants

Reaction Steps

To a solution of 4-bromo-6-(trifluoromethyl)-1H-indole (1 g, 3.79 mmol) in DMF (6 mL) was added 60% sodium hydride (0.182 g, 4.54 mmol), and the mixture was stirred for 30 min. 2-bromopropane (0.533 mL, 5.68 mmol) was added and the mixture was stirred overnight. The reaction was then quenched with 10% NaHCO3 and extracted with EtOAc (3×). The extract was dried over Na2SO4 and concentrated. The residue was purified using column chromatography (Silica gel, 0 to 100% EtOAc/hexanes) to give the title compound (460 mg, 40%) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.56-1.61 (m, 6 H), 4.66-4.79 (m, 1 H), 6.65 (d, J=3.03 Hz, 1 H), 7.27-7.31 (m, 1 H), 7.45 (d, J=3.03 Hz, 1 H), 7.54 (s, 1 H), 7.63 (s, 1 H). MS: (M+H)+=306.2.

Provenance & Evidence