تفاعل #49591

معادلة التفاعل

water

diethyl zinc toluene

4-Chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone

→

4-chloro-5-ethyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone

المردود 52.0%

المذيبات

dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   ترشيحfiltered
2. 2
   استخلاصThe filtrate was extracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with saturated brine
4. 4
   تجفيفby drying over sodium sulfate
5. 5
   أخرىThe solvent was evaporated under reduced pressure
6. 6
   أخرىthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=6/1)

الإجراء التجريبي

4-Chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (93.5 mg, 0.149 mmol) was dissolved in dimethoxyethane (4.7 mL), and the solution was added with 1.1 mmol/L diethyl zinc-toluene solution (0.68 mL, 0.744 mmol) and [bis(diphenylphosphino)ferrocene]dichloropalladium (34.4 mg, 0.030 mmol), followed by stirring at 90° C. for 12 hours under argon atmosphere. The reaction mixture was added with water and filtered using Celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=6/1) to obtain 4-chloro-5-ethyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (39.0 mg, yield 52%).

المصدر