4-Fluoroaniline → 5-Bromo-N-(4-fluorophenyl)pyridin-2-amine

Participants

Reaction Steps

5 g (21.1 mmol) of 2,5-dibromopyridine, 4.4 ml of 4-fluoroaniline, 4.10 g (42.3 mmol) of sodium-tert-butanolate, 200 mg (0.8 mmol) of palladium(II)acetate and 200 mg (0.3 mmol) of R-(+)-BINAP were dissolved in 60 ml of dioxane and stirred at reflux temperature for 1 h. The mixture was poured into ice-water and extracted with ethyl acetate. The organic phases were dried and evaporated, and the residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate 5:2). Yield: 2.10 g.

Provenance & Evidence