Reacción #53781

Ecuación de reacción

Sodium triacetoxyborohydride

Methyl 4-formylbenzoate

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

sodium bicarbonate

acetic acid

→

product

Rendimiento 26.7%

4-{[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenylamino]-methyl}-benzoic acid methyl ester

Rendimiento 26.7%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe resulting homogeneous solution stirred at room temperature for 4 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 brown gum
8. 8
   OtroRecrystallization from methanol

Procedimiento

Methyl 4-formylbenzoate (0.21 g, 1.28 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.34 g, 1.24 mmol) in methylene chloride (125 mL), followed by acetic acid (0.3 g, 3.33 mmol). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.3 g, 1.42 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 4 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 brown gum. Recrystallization from methanol gave the product as off-white crystals (140 mg), mp 168-170° C.

Fuente