反应详情

温度

60 °C

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.

1. stirringstirred at room temperature for 24 h
2. customThe reaction was quenched by 1 M HCl (5 ml)
3. stirringstirred at room temperature for 4 h
4. extractionthe product was extracted with EtOAc
5. customThe layers were separated
6. washthe organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under vacuum
9. customThe residue was purified by flash chromatography on silica gel eluting with 0-30% EtOAc-hexanes