反应详情

6-Bromo-5-fluoro-1H-indole (10 g, 46.7 mmol) was dissolved in DMF (100 mL) and cooled to 0° C. in an ice bath before the addition of sodium hydride, 60% dispersion in mineral oil (3.74 g, 93 mmol) and methyl 2-bromoacetate (8.59 mL, 93 mmol). The ice bath was removed and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was cooled with an ice bath once again then quenched with water (50 mL). The aqueous layer was extracted with DCM (3×200 mL). The organics were combined, passed through a hydrophobic frit and concentrated. The residue was purified by column chromatography on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to afford the title compound (10.209 g). LCMS (A): m/z (M+H)+ 286/288, C11H9BrFNO2 requires 285/287 (acidic).

1. customThe ice bath was removed
2. temperatureThe reaction mixture was cooled with an ice bath once again
3. customquenched with water (50 mL)
4. extractionThe aqueous layer was extracted with DCM (3×200 mL)
5. concentrationconcentrated
6. customThe residue was purified by column chromatography on silica gel
7. washeluting with a gradient of 0-40% ethyl acetate in cyclohexane