2-amino-4-fluoro-N-methylbenzamide → 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-4-fluoro-N-methyl-benzamide

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2-amino-4-fluoro-N-methylbenzamide (2.310 g, 13.74 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (3.5 g, 9.16 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.530 g, 0.92 mmol) diacetoxypalladium (0.103 g, 0.46 mmol) and cesium carbonate (5.97 g, 18.32 mmol) were suspended in dioxane (40 mL). The reaction was degased, purged with argon (3 times) and heated to 100 °C for 5 hours. The reaction mixture was allowed to cool to room temperature under stirring, diluted with ethyl acetate and the insolubles were removed by filtration, washed with EtOAc and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% methanol in ethyl acetate/DCM (1/1). Fractions containing pure product were evaporated to give a foam. This residue was triturated with DCM and filtered to afford EN03299-43-01 (1.4 g, 3.31 mmol, 36.2 %) as an off- white product. combined with APE-03299-48 700 mg of aniline was recovered

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