Реакция #49305

Уравнение реакции

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

Выход 70.0%

Растворители

acetonitrile

water

Условия реакции

Обработка

1. 1
   ЭкстракцияThe mixture was extracted with ethyl acetate
2. 2
   ПромывкаThe organic layer was washed with saturated brine
3. 3
   Сушкаdried over anhydrous sodium sulfate
4. 4
   ДругоеThe solvent was evaporated under reduced pressure

Методика

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%).

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