2,6-Dibromopyridine → 3-[(6-Bromopyridin-2-yl)methyl]-4-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(bromomethyl)-4-fluorobenzonitrile (from Step A above, 17.7 g, 83.3 mmol) in THF was cooled to 0° C. and then 160 mL of Zn/THF solution (124.4 mmol) was added. After stirring at 0° C. for 45 minutes, the reaction was stirred at ambient temperature for an additional 20 minutes. To this reaction mixture was added 2,6-dibromo pyridine (19.73 g, 83.3 mmol) and tetrakis(triphenylphosphine)palladium (5.00 g, 4.30 mmol), and heated to 90° C. for 1.5 hours until the reaction was complete by TLC. The reaction was cooled to room temperature, filtered through celite, and concentrated. The crude residue was purified via silica gel chromatography (hexanes/methylene chloride) to give the title compound (8.34 g).

Provenance & Evidence