Potassium Carbonate → [4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 5 of example 3. Thus, 4-(1-benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol (0.295 g, 0.662 mmol) was reacted with K2CO3 (0.110 g, 0.794 mmol) and bromoacetonitrile (0.095 g, 0.794 mmol) in acetone (10 ml) to give the product (0.265 g, 0.547 mmol, 83%) as a waxy solid, mp 97-99° C. 1H NMR (DMSO-d6) δ 0.72 (t, J=7.0 Hz, 3H), 1.11-1.19 (m, 4H), 1.47-1.57 (m, 2H), 2.65 (t, J=7.6 Hz, 2H), 5.16 (s, 2H), 5.24 (s, 2H), 6.80 (d, J=6.7 Hz, 2H), 7.10-7.18 (m, 5H), 7.32-7.48 (m, 7H), 7.64 (d, J=8.9 Hz, 2H), 7.75 (s, 1H); [ESI(+)], m/z 486 (M+H)+.

Provenance & Evidence