Tetrahydrofuran (10 mL) was cooled to −78° C. and tert-Butyllithium (4.56 ml, 6.84 mmol) was added, followed by a solution of 2-bromo-3-fluoro-6-methylpyridine (1 g, 5.26 mmol) in tetrahydrofuran (2.5 mL). The reaction mixture was stirred for 30 minutes then zinc(II)chloride (2.58 g, 18.95 mmol) was added and the reaction was warmed to room temperature over 2 hours. A solution of 2-(2-bromopyridin-4-yl) isoindoline-1,3-dione (9) (1.595 g, 5.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.608 g, 0.526 mmol) in THF (10 mL) was added and the reaction was stirred at room temperature over night to give a solid which was collected by filtration to give 2-(3′-fluoro-6′-methyl-2,2′-bipyridin-4-yl)isoindoline-1,3-dione as a white solid (786 mg).
