تفاعل #49305

معادلة التفاعل

4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

sodium carbonate

isonipecotamide

acetic acid

sodium triacetoxyborohydride

→

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

المردود 70.0%

المذيبات

acetonitrile

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture was extracted with ethyl acetate
2. 2
   غسيلThe organic layer was washed with saturated brine
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   أخرىThe solvent was evaporated under reduced pressure

الإجراء التجريبي

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (40.0 mg, 0.0974 mmol) was dissolved in acetonitrile (3 mL), and the solution was treated with isonipecotamide (154 mg, 1.20 mmol), acetic acid (0.896 mL, 15.7 mmol) and sodium triacetoxyborohydride (188 mg, 0.887 mmol). The reaction mixture was added with water and sodium carbonate to adjust the pH to 9. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(4-methoxycarbonylpiperidinomethyl)indol-2-yl]isoindolinone (35.5 mg, yield 70%).

المصدر