CONC(=O)c1ccc(F)cc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CONC(=O)c1ccc(F)cc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (24.98 mg, 0.04 mmol), diacetoxypalladium (5.82 mg, 0.03 mmol), 2-amino-4-fluoro-N- methoxybenzamide (90 mg, 0.49 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (110 mg, 0.29 mmol) and cesium carbonate (188 mg, 0.58 mmol) were weighed out in a µwave vial, sealed and dioxane (3 mL) was added. Argon was let to bubble in the mixture for 5 minutes. The reaction was stirred at 95 °C for 6h. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane, silica gel was added and the mixture was concentrated. The crude product was purified by flash chromatography on silica gel (25g) eluting with 0 to 5% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness. The residue was triturated in tBuOMe (a bit soluble and soluble in diethyl ether) and the resulting precipitate was collected by filtration and dried to a constant weight to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-4-fluoro- N-methoxybenzamide (50.0 mg, 39.6 %) as a white solid.
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