反应详情

To a stirred solution of N-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}benzamide (1.7 g in 130 mL dry tetrahydrofuran) was added 35 mL of a IM solution of borane in tetrahydrofuran and the mixture heated slowly to reflux on an oil bath. After 2 hours the mixture was cooled to room temperature and the excess borane quenched by the careful addition of methanol. The mixture was concentrated to half-volume, treated with N,N-dimethylethanolamine (13 mL) and heated to reflux on an oil bath. After 3 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol, 97:3) gave the title compound (1.5 g).

1. temperaturethe mixture heated slowly
2. temperatureto reflux on an oil bath
3. customthe excess borane quenched by the careful addition of methanol
4. concentrationThe mixture was concentrated to half-volume
5. additiontreated with N,N-dimethylethanolamine (13 mL)
6. temperatureheated
7. temperatureto reflux on an oil bath
8. temperatureAfter 3 hours the mixture was cooled to room temperature
9. concentrationconcentrated in vacuo
10. customPurification by flash chromatography on silica gel (methylene chloride:methanol, 97:3)