反应详情

3.5 g (8 mmol) of 1-tert-butoxycarbonyl-2-methylindol-5-yl-carboxylic acid-N-phenyl-N-(2-methoxycarbonylethyl)amide were dissolved in 80 mL of carbon tetrachloride, mixed with 1.5 g (8.4 mmol) of N-bromosuccinimide and 20 mg of azobisisobutyronitrile and refluxed for 2.5 hours. Then the still warm solution was filtered, the filtrate obtained was washed with saturated sodium hydrogen carbonate solution and dried with sodium sulfate. After distillation of the solvent, the crude product was dissolved in 30 mL of N-ethyldiisopropylamine, mixed with 1.0 g (8 mmol) of 4-aminobenzonitrile and refluxed for 2.5 hours. The solvent was distilled off in vacuo and the residue obtained was purified by chromatography (silica gel; ethyl acetate/petroleum ether=1:4 to 1:1). Yield: 1.1 g (30% of theory); Rf value: 0.21 (silica gel; ethyl acetate/petroleum ether=1:1).

1. temperaturerefluxed for 2.5 hours
2. filtrationThen the still warm solution was filtered
3. customthe filtrate obtained
4. washwas washed with saturated sodium hydrogen carbonate solution
5. dry with materialdried with sodium sulfate
6. distillationAfter distillation of the solvent
7. dissolutionthe crude product was dissolved in 30 mL of N-ethyldiisopropylamine
8. temperaturerefluxed for 2.5 hours
9. distillationThe solvent was distilled off in vacuo
10. customthe residue obtained
11. customwas purified by chromatography (silica gel; ethyl acetate/petroleum ether=1:4 to 1:1)