反应详情

The crude 4-bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzonitrile (3.04 g) dissolved in dry tetrahydrofuran (50 mL) was dropped to an ice-cold slurry of lithium aluminium hydride 4.16 g, 0.11 mmol) in dry tetrahydrofuran (50 mL). The mixture was stirred for 1 h at ambient temperature, and then heated at reflux for another hour. The flask was cooled on ice, and the reaction mixture quenched with water (4.2 mL) followed by 15% NaOH(aq) (4.2 mL). Additional water (12.6 mL) was added and the mixture stirred at ambient temperature for 1 h. The white precipitate was filtered and washed with tetrahydrofuran. Evaporation afforded crude 4-bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzylamine (3.20 g) as a yellow oil. This was stirred together with ethyl trifluoroacetate (2.5 ml, 20.9 mmol) in dry methylene chloride (50 mL) for 17 h at room temperature. Evaporation followed by chromatography (ethyl acetate/heptane: 25/75) gave the sub-title compound.

1. temperatureheated
2. temperatureat reflux for another hour
3. temperatureThe flask was cooled on ice
4. customthe reaction mixture quenched with water (4.2 mL)
5. additionAdditional water (12.6 mL) was added
6. stirringthe mixture stirred at ambient temperature for 1 h
7. filtrationThe white precipitate was filtered
8. washwashed with tetrahydrofuran
9. customEvaporation