To a solution of 4-(2-chloropyridin-4-yloxy)-3,5-difluoroaniline (3.0 g, 11.7 mmol) in a mixture of N,N-dimethyl-formamide and water (v/v=3:1, 80 mL) was added 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (3.6 g, 17.5 mmol), potassium phosphate (4.9 g, 23.4 mmol) and tetrakis(triphenylphosphine) palladium (0.7 g, 0.6 mmol). The mixture was degassed thoroughly, heated to 100° C. and stirred under nitrogen overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography to give 3,5-difluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)aniline (2.6 g, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.36 (d, J=5.6 Hz, 1H), 8.28 (s, 1H), 7.98 (s, 1H), 7.24 (d, J=2.4 Hz, 1H), 6.64 (dd, J=5.6 Hz, J=2.4 Hz, 1H), 6.37 (d, J=10.8 Hz, 2H), 5.81 (s, 2H), 3.87 (s, 3H); MS (ESI): m/z 303.1 [M+H]+.
