反応 #53808

反応方程式

sodium bicarbonate

4-Hydroxy-3-nitrobenzaldehyde

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

Sodium triacetoxyborohydride

→

product

収率 35.3%

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

収率 35.3%

溶媒

methylene chloride

acetic acid

反応条件

後処理

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
   その他the organic layer separated
5. 5
   乾燥dried over Na2SO4
6. 6
   その他The solvent was evaporated
7. 7
   その他to give an orange solid
8. 8
   その他Recrystallization from methanol

実験手順

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.

出典