Sodium Carbonate → methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

Participants

Reaction Steps

A solution (0.04 M) of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in WO2004/087714) in DME/EtOH 5:2 was treated with [2-(hydroxymethyl)phenyl]boronic acid (1.2 eq), Na2CO3 (6 eq) and Pd(PPh3)4 (0.1 eq) at 80° C. After 1 h the mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, then dried and concentrated under reduced pressure. The residue was purified by flash chromatography on SiO2 (7:3 PE/EtOAc) to give the title compound (93%) as a solid. MS (ES+) m/z 364 (M+H+).

Provenance & Evidence