Reaktion #49300

Reaktionsgleichung

sodium carbonate

N,N-dimethylamine hydrochloride

triethylamine

acetic acid

sodium triacetoxyborohydride

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

→

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

Ausbeute 117.7%

Lösungsmittel

ethyl acetate

water

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThen, the mixture was extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure

Vorschrift

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (30.0 mg, 0.0730 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with N,N-dimethylamine hydrochloride (120 mg, 1.47 mmol), triethylamine (0.162 mL, 1.17 mmol), acetic acid (0.084 mL, 1.5 mmol) and sodium triacetoxyborohydride (154 mg, 0.727 mmol). The reaction mixture was added with water and ethyl acetate. The mixture was added with sodium carbonate to adjust the pH to 9. Then, 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-(dimethylaminomethyl)indol-2-yl]isoindolinone (37.8 mg).

Quelle