反应详情

LAH (1.0M in THF, 5.75 mL, 5.75 mmol) was added dropwise to refluxing 4-bromo-1H-indole-3-carbaldehyde (644 mg, 2.87 mmol; Intermediate 27) in dry THF (20 mL). The mixture was refluxed 1 h, allowed to attain rt. and quenched with water (220 μL), W/w 15% aq. NaOH (220 μL) and water (650 μL). The resulting precipitation was filtered off, the filtrate concentrated and the residue was extracted with aq. NaOH (10 mL) and DCM (2×10 mL). The organic layers were combined with combined with an earlier batch of this intermediate (followed this experimental and starting from 4-bromo-1H-indole-3-carbaldehyde, 100 mg, 0.45 mmol; Intermediate 27), dried and concentrated to give the title compound (556 mg, 80%) as a light brown oil. MS (ESI+) for C9H8BrN m/z 210 (M+H)+.

1. temperatureThe mixture was refluxed 1 h
2. customto attain rt
3. customand quenched with water (220 μL), W/w 15% aq. NaOH (220 μL) and water (650 μL)
4. customThe resulting precipitation
5. filtrationwas filtered off
6. concentrationthe filtrate concentrated
7. extractionthe residue was extracted with aq. NaOH (10 mL) and DCM (2×10 mL)
8. dry with materialIntermediate 27), dried
9. concentrationconcentrated