3,4-Difluorobenzaldehyde → HCID 24753616, compound

Participants

Reaction Conditions

Reaction Steps

General Procedure G. To a solution of 1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)ethanone (Compound 29, 64 mg, 0.21 mmol) in EtOH (3 ml) and NaOH (4 M, 0.53 ml) at room temperature was added 3,4-difluorobenzaldehyde (46 μl, 0.42 mmol). The reaction was stirred for 16 h, heated to 60° C. for 4 h, and more 3,4-difluorobenzaldehyde (180 μl, 1.68 mmol) was added, stirred at room temperature for 24 h. The reaction was quenched by 1 M HCl (5 ml), and stirred at room temperature for 4 h, and the product was extracted with EtOAc. The layers were separated and the organic layer was washed with brine, and dried over Na2SO4, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 0-30% EtOAc-hexanes followed by PTLC (30% EtOAc-hexanes) to yield (E)-1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)-3-(3,4-difluorophenyl)prop-2-en-1-one (Compound 30) as a yellow solid.

Provenance & Evidence