CONC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1cc(N)n(C(C)C)n1>C1COCCO1.CC(=O)O.CC(=O)O.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C(C)C)ncc1Cl2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and cesium carbonate (626 mg, 1.92 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (120 mg, 0.19 mmol) and diacetoxypalladium (21.58 mg, 0.10 mmol) were added and tube was sealed. Mixture was stirred at reflux overnight. Reaction was allowed to cool to room temperature, filtered, washed with CH2Cl2/MeOH (9/1, 10 mL) and concentrated to dryness. The crude product was purified by flash chromatography (dry loading) on silica gel eluting with 1 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(5-chloro-2-(1-isopropyl-3-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-N-methoxybenzamide (98 mg, 36.9 %) as a pink foam => _impure, contains BINAP or BINAP by- products_
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