Benzyl Bromide → 1-Benzyl-5-bromo-3-pentyl-2-phenyl-1H-indole

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 5-bromo-3-pentyl-2-phenyl-1H-indole (1.711 g, 5 mmol) was reacted with k-t-butoxide (0.589 g, 5.25 mmol) and benzyl bromide (0.901 g, 5.25 mmol) in DMF (15 ml) to give the product (1.285 g, 2.972 mmol, 59%) as a white solid, mp 98-101° C. 1H DMSO-d6) δ 0.75 (t, J=7.0 Hz, 3H), 1.11-1.19 (m, 4H), 1.46-1.52 (m, 2H), 2.60 (t, J=7.5 Hz, 2H), 5.25 (s, 2H), 6.77-6.78 (m, 2H), 7.13-7.22 (m, 4H), 7.32 (d, J=8.7 Hz, 1H), 7.34-7.36 (m, 2H), 7.42-7.49 (m, 3H), 7.75 (d, J=1.8 Hz, 1H); [ESI(+)], m/z 432/434 (M+H)+.

Provenance & Evidence