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

Participants

Reaction Conditions

Reaction Steps

[3-(acetylamino)-2-aminophenyl]boronic acid (prepared as described in Example 5, Step 1 above) (1.1 eq) was added to a solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared from commercially available methyl indole-6-carboxylate as described in WO 2004/087714) in dioxane (0.06 M). 2M aqueous Na2CO3 (4 eq) was introduced and the mixture degassed by sonication under a N2 atmosphere prior to introducing bis(triphenylphosphine)palladium(II) dichloride (0.2 eq) and heating at 105° C. for 2 h. The reaction was allowed to cool to RT before partitioning between EtOAc and water. The aqueous phase was extracted a second time with EtOAc and the combined organics washed with water, brine before being dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography (5% MeOH/CH2Cl2) afforded the title compound as a glass (59%). MS (ES+) m/z 406 (M+H)+.

Provenance & Evidence