Réaction #49306

Équation de réaction

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

hydrochloric acid

ethylamine

acetic acid

sodium triacetoxyborohydride

→

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

Rendement 83.0%

Solvants

acetonitrile

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Extractionby extracting with 1 mol/L hydrochloric acid
2. 2
   workup.ADDITIONThe aqueous layer was added with sodium hydrogen carbonate
3. 3
   ExtractionThe mixture was extracted with ethyl acetate
4. 4
   LavageThe organic layer was washed with saturated brine
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   AutreThe solvent was evaporated under reduced pressure

Mode opératoire

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (41.2 mg, 0.100 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 70% aqueous ethylamine-solution (0.192 mL, 2.42 mmol), acetic acid (0.345 mL, 6.03 mmol) and sodium triacetoxyborohydride (170 mg, 0.802 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and ethyl acetate, followed by extracting with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium hydrogen 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-(ethylaminomethyl)indol-2-yl]isoindolinone (36.4 mg, yield 83%).

Source