Reaktion #53807

Reaktionsgleichung

sodium bicarbonate

3-Hydroxy-4-nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

Ausbeute 41.1%

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

Ausbeute 41.1%

Lösungsmittel

methylene chloride

acetic acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

3-Hydroxy-4-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 (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 3 days. Saturated aqueous sodium bicarbonate solution (100 mL), was added and the mixture was stirred for 2 hours. The mixture was shaken; the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give a red-orange gum. Recrystallization from methanol gave the product (350 mg), mp 170-171° C.

Quelle