Reaction #53806

Reaction equation

sodium bicarbonate

4-Nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

Yield 55.0%

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

Yield 55.0%

Solvents

methylene chloride

acetic acid

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting homogeneous solution was stirred at room temperature for 6 days
2. 2
   workup.STIRRINGthe mixture was stirred for 2 hours
3. 3
   workup.STIRRINGThe mixture was shaken
4. 4
   Otherthe organic layer was separated
5. 5
   Dryingdried over Na2SO4
6. 6
   OtherThe solvent was evaporated
7. 7
   Otherto give a red solid
8. 8
   OtherRecrystallization from methanol

Procedure

4-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 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 6 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 solid. Recrystallization from methanol gave the product (450 mg), mp 181-182° C.

Source