3-Methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole

35081-45-9

51388-20-6

198479-63-9

General procedure for the synthesis of 3-methyl-5-benzyloxy-2-(4-benzyloxyphenyl)-1H-indole from 4'-benzyloxy-2-bromophenyl acetone and 4-benzyloxyaniline hydrochloride: 10 g of 4'-benzyloxy-2-bromophenyl acetone (II-a), 15 g of p-benzyloxyaniline hydrochloride (II-b), 50 mL of N,N-dimethylformamide and 8 mL of triethylamine were mixed and reacted at 115 °C for 4 hours. Upon completion of the reaction, the progress of the reaction was monitored by thin layer chromatography (TLC). The reaction solution was slowly poured into 250 mL of ice water and a solid was precipitated. The crude product was collected, washed with 20 mL of methanol and dried under vacuum at 40 °C for 24 h. 12.5 g of yellow-brown solid product, 5-benzyloxy-2-[(4-benzyloxy)phenyl]-3-methyl-1H-indole (Intermediate II), was obtained in 94.6% yield.