A solution of 5-bromo-3-methylpyridin-2-amine (120a, 1.87 g, 10.0 mmol) in toluene (60 mL) was treated with 4-(dimethylamino)phenylboronic acid (2.48 g, 15.0 mmol), Pd(PPh3)4 (345 mg, 0.30 mmol), and 2M Na2CO3(aq) (10 mL). The reaction mixture was heated to reflux for 18 hours and then cooled to room temperature. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5-(4-(dimethylamino)phenyl)-3-methylpyridin-2-amine (120b).
