4-Nitrobenzaldehyde → [5-(1H-Indol-2-yl)-2-methoxy-phenyl]-(4-nitro-benzyl)-amine

4-Nitrobenzaldehyde (0.302 g, 2.0 mmol) was added to a stirred mixture of 5-(1H-indol-2-yl)-2-methoxy-phenylamine (0.476 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 was stirred at room temperature for 4 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture was stirred for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give an orange solid. Recrystallization from ethyl acetate gave the product (290 mg), mp 198-199° C.

1. stirringthe resulting homogeneous solution was stirred at room temperature for 4 days
2. stirringthe mixture was stirred for 2 hours
3. stirringThe mixture was shaken
4. customthe organic layer was separated
5. dry with materialdried over Na2SO4
6. customThe solvent was evaporated
7. customto give an orange solid
8. customRecrystallization from ethyl acetate

ORD record

ord-cebbfcc888aa4162b8abe136e3ae7d6b

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06858739B2