تفاعل #53809

معادلة التفاعل

sodium bicarbonate

4-Cyanobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

المردود 38.5%

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

المردود 38.5%

المذيبات

methylene chloride

acetic acid

ظروف التفاعل

المعالجة

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
   أخرىthe organic layer separated
5. 5
   تجفيفdried over Na2SO4
6. 6
   أخرىThe solvent was evaporated
7. 7
   أخرىto give a colorless gum
8. 8
   أخرىRecrystallization from methanol

الإجراء التجريبي

4-Cyanobenzaldehyde (0.262 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 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 colorless gum. Recrystallization from methanol gave the product (300 mg), mp 158-159° C.

المصدر