تفاعل #53808

معادلة التفاعل

sodium bicarbonate

4-Hydroxy-3-nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

المردود 35.3%

[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl](4-hydroxy-3-nitro-benzyl)-amine

المردود 35.3%

المذيبات

methylene chloride

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting homogeneous solution stirred at room temperature for 7 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 an orange solid
8. 8
   أخرىRecrystallization from methanol

الإجراء التجريبي

4-Hydroxy-3-nitrobenzaldehyde (0.334 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 (0.47 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 7 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 an orange solid. Recrystallization from methanol gave the product (300 mg), mp 195-196° C.

المصدر