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

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 1 of example 4. Thus, 4-(1-benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol (0.300 g, 0.673 mmol) was reacted with K2CO3 (0.121 g, 0.875 mmol) and methyl bromoacetate (0.134 g, 0.875 mmol) in acetone (10 ml) to give the product (0.296 g, 0.572 mmol, 85%) as a white, waxy solid, mp 106-109° C. 1H NMR (DMSO-d6) δ 0.72 (t, J=7.0 Hz, 3H), 1.09-1.19 (m, 4H), 1.49-1.56 (m, 2H), 2.64 (t, J=7.5 Hz, 2H), 3.68 (s, 3H), 4.79 (s, 2H), 5.23 (s, 2H), 6.79-6.81 (m, 2H), 6.97 (d, J=8.9 Hz, 2H), 7.09-7.18 (m, 3H), 7.29-7.34 (m, 4H), 7.37-7.47 (m, 3H), 7.55 (d, J=8.9 Hz, 2H), 7.72 (d, J=0.7 Hz, 1H); [ESI(+)], m/z 519 (M+H)+.

Provenance & Evidence