反应详情

A mixture of ethyl 6-bromo-1H-indole-2-carboxylate (2.5 g) and 4-methylphenylboric acid (1.39 g), potassium carbonate (2.58 g) and toluene/ethanol/water (90/9/9 ml) was stirred at room temperature for one hour. Into the reaction mixture was added tetrakis(triphenylphosphine)palladium (0.32 g), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane 1:5→1:2→1:1) and to recrystallization (ethyl acetate/hexane) to obtain ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate (1.92 g) as colorless crystals.

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 18 hours
3. temperatureAfter cooling to room temperature
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
6. dry with materialwas dried with magnesium sulfate
7. concentrationAfter concentration under reduced pressure
8. customthe residue was subjected to purification
9. customto recrystallization (ethyl acetate/hexane)