To a flask were weighed 5-bromo-2-methoxypyridin-3-amine, 11.1.A, (1 g, 4.9 mmol), pyridin-4-ylboronic acid (0.73 g, 5.9 mmol), X-Phos (0.47 g, 0.99 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.22 g, 0.25 mmol), and Potassium phosphate tribasic (3.13 g, 14.8 mmol). N-butanol was added as a solvent and the reaction mixture was heated at 110° C. for 3 hr. The solids were filtered off through a pad of celite. The filtrate was concentrated and chromatographed by gradient EtOAc/DCM and then 10% MeOH/DCM to afford 730 mg of 11.1.B (74%).
