3-Nitrobenzaldehyde → [5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-(3-nitrobenzyl)-amine

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Reaction Steps

3-Nitrobenzaldehyde (0.3 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 is 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 6 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture was sired for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give a yellow solid. Recrystallization from methanol gave the product (220 mg), mp 212-214° C.

Provenance & Evidence