Ethanol → HCID 86698628, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy]-2,2-dimethylpropan-1-ol (60 mg, 0.21 mmol) in toluene (6 mL) was added 5-bromo-6-chloro-1H-indole-3-carbaldehyde (64 mg, 0.25 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (15 mg, 0.021 mmol), 2M aqueous potassium carbonate (0.42 mL, 0.84 mmol) and ethanol (2 mL). The reaction mixture was degassed with nitrogen for 3 min and heated to 110° C. by microwave irradiation for 1 h. The cooled reaction mixture was concentrated in vacuo to give a residue, which was dissolved with ethyl acetate (30 mL) and washed with brine (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a residue, which was purified by flash chromatography to give 6-chloro-5-[4-(3-hydroxy-2,2-dimethylpropoxy)phenyl]-1H-indole-3-carbaldehyde (60 mg, 82%) as an off-white solid.

Provenance & Evidence