4-Chlorobenzylamine → (4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

Participants

Reaction Conditions

Reaction Steps

To 2,6-difluoro-pyridine (20, 3.80 g, 33.0 mmol) in 20.0 mL ofN-methylpyrrolidone, 4-chloro-benzylamine (21, 5.6 mL, 46.0 mmol) and N,N-diisopropylethylamine (10.0 mL, 57.4 mmol) were added. The reaction was stirred at 90° C. overnight, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 25% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum, and the resulting material was washed with ethyl acetate/hexane to provide the desired compound as a white solid (22, 5.30 g).

Provenance & Evidence