Potassium Carbonate → HCID 86698607, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of crude 1-{3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]pyrrolidin-1-yl}ethanone (assume 0.38 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (98.4 mg, 0.38 mmol) and 2N aqueous potassium carbonate (0.76 mL, 1.52 mmol) in toluene (2.25 mL) and ethanol (0.75 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (27.8 mg, 0.038 mmol). The reaction mixture was heated to 110° C. in a microwave for 30 minutes. After cooling to room temperature, the reaction mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column (first EtOAc in Petroleum ether, then MeOH in CH2Cl2) to give 5-[4-(1-acetylpyrrolidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (52 mg) as an orange solid. MS (ES+) 389.0 (M+Na)+

Provenance & Evidence