Reacción #53780

Ecuación de reacción

Sodium triacetoxyborohydride

4-Methoxybenzaldehyde

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

sodium bicarbonate

acetic acid

→

product

Rendimiento 46.3%

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

Rendimiento 46.3%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe resulting homogeneous solution stirred at room temperature for 3 days
2. 2
   workup.STIRRINGthe mixture stirred for 2 hours
3. 3
   workup.STIRRINGThe mixture was shaken
4. 4
   Otrothe organic layer separated
5. 5
   Secadodried over Na2SO4
6. 6
   OtroThe solvent was evaporated
7. 7
   Otroto give a yellow oil
8. 8
   OtroRecrystallization from methanol/water

Procedimiento

4-Methoxybenzaldehyde (0.204 g, 1.5 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.405 g, 1.48 mmol) in methylene chloride (125 mL), followed by acetic acid (0.3 g, 1.5 mmol). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.31 g, 1.46 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 3 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 a yellow oil. Recrystallization from methanol/water gave the product as off-white crystals (270 mg); mp 173-175° C.

Fuente