Reaktion #53808

Reaktionsgleichung

sodium bicarbonate

4-Hydroxy-3-nitrobenzaldehyde

5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine

Sodium triacetoxyborohydride

→

product

Ausbeute 35.3%

[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl](4-hydroxy-3-nitro-benzyl)-amine

Ausbeute 35.3%

Lösungsmittel

methylene chloride

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting homogeneous solution stirred at room temperature for 7 days
2. 2
   workup.STIRRINGthe mixture stirred for 2 hours
3. 3
   workup.STIRRINGThe mixture was shaken
4. 4
   Sonstigethe organic layer separated
5. 5
   Trocknendried over Na2SO4
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Sonstigeto give an orange solid
8. 8
   SonstigeRecrystallization from methanol

Vorschrift

4-Hydroxy-3-nitrobenzaldehyde (0.334 g, 2.0 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.548 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.47 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 7 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture stirred for 2 hours. The mixture was shaken, the organic layer separated and dried over Na2SO4. The solvent was evaporated to give an orange solid. Recrystallization from methanol gave the product (300 mg), mp 195-196° C.

Quelle