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) (76 mg, 0.13 mmol) and diacetoxypalladium (14.77 mg, 0.07 mmol) were dissolved in dioxane (15 mL) and argon was let to bubble in the mixture for 5 minutes. 2-amino-N- methylbenzamide (336 mg, 2.24 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (503 mg, 1.32 mmol) and cesium carbonate (858 mg, 2.63 mmol) were added and the reaction was heated to 90 °C, over a period of 90 minutes under nitrogen. LCMS didn't show a complete clean reaction (as Cs2CO3 got stuck on the flask). Vigourous stirring was applied and theaction was heated to 90 °C, over a period of 90 minutes under nitrogen. Crude LCMS was as expected. The reaction mixture was allowed to cool to room temperature under stirring, diluted with dichloromethane and decalite speed + was added. The mixture was concentrated and the crude product was purified by flash chromatography on silica gel eluting with 0 to 5% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness, giving a gummy foam of P1 (490mg). A bit of diethyl ether then a lot of pentane were added to obtain a solid, which was dried under vacuum at 50°C to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (450 mg, 77 %) as an yellow solid.

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