反应详情

To a solution of sodium hydride (60%, 254 mg, 6.35 mmol) in 15 mL tetrahydrofuran (THF) was added 5-allyloxyindole (Step A; 1.0 g, 5.77 mmol) in 5 mL THF and the mixture was stirred for 1 hour at ambient temperature. 4-fluorochlorobenzene (0.69 mL, 6.35 mmol) was added and the reaction heated to reflux for 21 hours. After cooling, the reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to provide the title compound.

1. temperaturethe reaction heated
2. temperatureto reflux for 21 hours
3. temperatureAfter cooling
4. customthe reaction was quenched with saturated aqueous ammonium chloride
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with water, brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customthe crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane)