2-Amino-N-methylbenzamide → 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide

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(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.606 g, 1.05 mmol), diacetoxypalladium (0.118 g, 0.52 mmol), 2-amino-N-methylbenzamide (2.67 g, 17.80 mmol) and N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (4 g, 10.47 mmol) were dissolved in dioxane (120 mL) and argon was let to bubble in the mixture for 5 minutes.cesium carbonate (6.82 g, 20.94 mmol) was added and argon was let to bubble in the mixture for 5 minutes. The reaction was stirred at 90 °C for 2 hours. After taking 2 aliquotsd to check the reaction it turned from yello to grey. LCMS didn't show a complete clean reaction but it stopped. The reaction mixture was allowed to cool to room temperature under stirring, diluted with dichloromethane, insoluble was removed by filtration and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel (150g) eluting with 0 to 5% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness, giving a gummy foam. 60 mL of tBuOMe was added and the resulting solution was stirred at rt for 15 minutes. The resulting precipitate was collected by filtration, washed with tBuOMe and dried to a constant weight to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (3.60 g, 85 %) as a pale beige solid.

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