2-amino-N-ethoxybenzamide → 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-ethoxybenzamide

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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-ethoxybenzamide (120 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 (~90% conversion)_. A few Pd(OAc)2, Xantphos and Cs2CO3 were added. Reaction was degassed with nitrogen and stirred at 90°C for 2 hours => _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 4% methanol in dichloromethane. Solvent was evaporated to afford product as a pale yellow foam. This was dissolved in Et2O, petroleum ether was added 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-ethoxybenzamide (127 mg, 74.5 %) as a white solid.

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