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

3-Hydroxy-4-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 (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 3 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 a red-orange gum. Recrystallization from methanol gave the product (350 mg), mp 170-171° C.

1. stirringthe resulting homogeneous solution was stirred at room temperature for 3 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 a red-orange gum
8. customRecrystallization from methanol

ORD record

ord-b794240a450847f7b2bbcba41b93927f

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06858739B2