反应详情

To a suspension of 1H-indole-3-carboxylic acid ethyl ester (800 mg, 4.23 mmol) and potassium carbonate (1.34 g, 9.72 mmol) in CH3CN (21 mL) under nitrogen was added tert-butyl bromoacetate (875 μL, 5.92 mmol) and the reaction mixture was heated at reflux overnight. The reaction mixture was allowed to cool to RT, EtOAc and water were added and the layers were separated, the aqueous one being re-extracted with EtOAc. The organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography (c-hexane to c-hexane/EtOAc 1:1) to afford the desired compound. TLC, Rf (EtOAc)=0.77; MS (LC/MS): 304.1 [M+H]+, 302.0 [M−H]−; tR (HPLC conditions a): 4.01 min.

1. temperaturethe reaction mixture was heated
2. temperatureat reflux overnight
3. customthe layers were separated
4. extractionthe aqueous one being re-extracted with EtOAc
5. washThe organic layers were washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude residue was purified by flash column chromatography (c-hexane to c-hexane/EtOAc 1:1)