2-[2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino]-N-methylbenzamide → N-methyl-2-[[2-[[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyridin-4-yl]amino]benzamide

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2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.30 mmol), 1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-amine hydrochloride (122 mg, 0.61 mmol), cesium carbonate (247 mg, 0.76 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.1 mg, 0.05 mmol) and diacetoxypalladium (5.45 mg, 0.02 mmol) were suspended in dioxane (1.5 mL) and sealed into a tube. The reaction was degased, purged with nitrogen and heated to 100 °C for 18 hours. Reaction was filtered. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford N-methyl-2-(2-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)benzamide (84 mg, 60.4 %) as a yellow crystalline solid.

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