Sodium hydride → HCID 21964287, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60%, 36.8 g, 921 mmol) was added portionwise to a stirring solution of 5-bromoindole (152.0 g, 768 mmol) in DMF (1.4 L) at 0° C. under a nitrogen atmosphere over a period of one hour. The mixture was stirred at 0° C. for one hour and at room temperature for 2.5 hours. 4-(tert-Butyl)benzyl bromide (180.0 g, 768 mmol) was added over a period of one hour. The mixture was stirred at room temperature for 3 hours. The reaction was quenched with aqueous ammonium chloride (5%, 1.4 L). The precipitated solid was isolated by filtration, washed with water (5×0.5 L), then with petroleum ether (0.3 L). The solid was dried in the air and then under vacuum at 60° C. for 18 hours to afford the title compound as a white solid (257 g, 97%), m.p. 108–109° C. Mass spectrum (ESI, [M+H]+) m/z 342. 1HNMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), δ 7.55 (s, 1H), δ 7.44 (d, 1H, J=8.71 Hz), 7.30 (d, 2H, J=7.96 Hz), 7.19 (d, 1H, J=8.71 Hz), 7.10 (d, 2H, J=7.63 Hz), 6.46 (s, 1H), 5.36 (s, 2H), and 1.21 ppm (s, 9H).

Provenance & Evidence