N-(1,3-dimethylpyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine → 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-(2-hydroxyethoxy)benzamide

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(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (22.71 mg, 0.04 mmol), diacetoxypalladium (4.41 mg, 0.02 mmol), 2-amino-N-(2-hydroxyethoxy)benzamide (131 mg, 0.67 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were weighed out in a µwave vial, sealed and dioxane (4 mL) was added. Reaction was degassed with nitrogen. The reaction was stirred at 90 °C for 12 hours => _incomplete (~85% conversion)_. A few Pd(OAc)2, Xantphos and Cs2CO3 were added. Reaction was degassed with nitrogen and stirred at 90°C for 2 hours => _almost complete._ The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane and MeOH and silica (40-63 µm) was added. Mixture was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 0 to 12% methanol in ethyl acetate. Solvent was evaporated to afford product as a yellow foam. This was triturated in Et2O and petroleum ether and the resulting precipitate was sonicated for 10 minutes. Solid was filtered and dried under high vacuum to afford 2-(2-(1,3-dimethyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-(2-hydroxyethoxy)benzamide (86 mg, 48.6 %) as a yellow solid.

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