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

Participants

Reaction Conditions

Reaction Steps

2-bromo-3-cyclohexyl indole-6-carboxylic acid methyl ester (1 eq., prepared as described in WO2004/087714 from commercially available methyl indole-6-carboxylate) was mixed with [2-(hydroxymethyl)phenyl]boronic acid (1.5 eq.) and bis(triphenylphosphine)palladium dichloride (0.2 eq.) was added. The mixture was degassed and dioxane and 2M aq. Na2CO3 solution (2 eq.) were added. The mixture was heated under N2-atmosphere to 110° C. for 1 h then diluted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was subjected to flash chromatography (PE:EtOAc, 4:1). After evaporation of the solvents the product was obtained as orange solid (95%). MS (ES+): 364.3 (M+H+).

Provenance & Evidence