2-Chloro-6-fluoro-4-iodobenzonitrile (291 mmol, 82 g), THF (800 ml) and 1-(tetra-hydro-2H-pyran-2-yl)-1H-pyrazole-5-boronic acid pinacol ester (350 mmol, 97 g) were added into a flask and stirred. Bis(triphenylphosphine)palladium(II) chloride (14.57 mmol, 10.22 g), sodium carbonate (699 mmol, 74.1 g) and water (350 ml) were added. The resulting mixture was heated to 60° C. and stirred for 2 h. The solvents were evaporated. Water was added and the mixture was left to stir overnight. EtOAc and water were added and the insoluble precipitates were removed by filtration. The organic phase was separated from the filtrate and the water phase was extracted with more EtOAc. The combined organics were evaporated and the residue was combined with previously filtrated solid. The collected solids were suspended in EtOH and water. The mixture was heated to boiling point, allowed to cool to RT and stirred for an hour at ambient temperature. The mixture was cooled to 0° C. and stirred for another hour. The precipitate was washed with a small amount of cold 1:1 water/EtOH. The filtered solids were dried under vacuum. 91.2 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.50-1.70 (m, 3H), 1.79-1.89 (m, 1H), 1.92-2.03 (m, 1H), 2.30-2.44 (m, 1H), 3.56-3.67 (m, 1H), 3.93-4.02 (m, 1H), 5.36 (dd, 1H), 6.78 (d, 1H), 7.66 (d, 1H), 7.73 (dd, 1H), 7.80-7.83 (m, 1H).
