تفاعل #49505

معادلة التفاعل

4-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

acetonitrile

water

→

4-cyano-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

المردود 83.0%

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate
2. 2
   غسيلThe organic layer was washed with saturated brine
3. 3
   تجفيفdried over sodium sulfate
4. 4
   أخرىThe solvent was evaporated under reduced pressure
5. 5
   أخرىThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=8/1)

الإجراء التجريبي

4-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (300 mg, 0.505 mmol) was dissolved in acetonitrile (15 mL), and the solution was added with zinc cyanide (178 mg, 1.52 mmol) and [bis(diphenylphosphino)ferrocene]dichloropalladium (33 mg, 0.0404 mmol), followed by stirring at 90° C. for 17 hours under argon atmosphere. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=8/1) to obtain 4-cyano-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (198 mg, yield 83%).

المصدر