Sodium Carbonate → HCID 86627906, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (3-formyl-2-methoxyphenyl) boronic acid (1.5 eq) and Pd(PPh3)2Cl2 (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with Ar. 2M Na2CO3 solution (1 eq) was added and the mixture was heated to 110° C. for 2 h. All volatiles were evaporated in vacuo and the residual material was dissolved in EtOAc, filtered over Celite and evaporated in vacuo. The residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1). After evaporation of the fractions containing product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate was obtained as off-white solid (77%). (ES+) m/z 392 (M+H)+.

Provenance & Evidence