Reaktion #53805

Reaktionsgleichung

sodium bicarbonate

3-Nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

Ausbeute 26.9%

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

Ausbeute 26.9%

Lösungsmittel

methylene chloride

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting homogeneous solution was stirred at room temperature for 6 days
2. 2
   workup.WAITthe mixture was sired 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 yellow solid
8. 8
   SonstigeRecrystallization from methanol

Vorschrift

3-Nitrobenzaldehyde (0.3 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 is 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 6 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture was sired for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give a yellow solid. Recrystallization from methanol gave the product (220 mg), mp 212-214° C.

Quelle