COc1cc2c(cc1N)N(C(C)=O)CC2.Cc1cnc(Cl)nc1-c1cnn2ccccc12>C1COCCO1.CC(=O)O.CC(=O)O.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COc1cc2c(cc1Nc1ncc(C)c(-c3cnn4ccccc34)n1)N(C(C)=O)CC2A mixture of 3-(2-chloro-5-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine (400 mg, 1.55 mmol), 1-(6-amino-5-methoxyindolin-1-yl)ethanone (341 mg, 1.55 mmol) and diacetoxypalladium (34.9 mg, 0.16 mmol) 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (97 mg, 0.16 mmol) cesium carbonate (759 mg, 2.33 mmol) were degassed with nitrogen then dioxane (7 mL) was added to mixture and the solution was degassed under vacuum and placed under nitrogen. The resulting suspension was stirred at 90 °C for 5hours. Control uplc/ms OK Control t.l.c : 100%EtOAc and 5%MeOH/CH2Cl2 After cooling, the mixture was filtered and the filtrate evaporated to dryness after addition of silica gel The crude product was purified by flash chromatography on silica gel 45g Merck column solid injectioneluting with 0 to 10%MeOH/EtOAc. The solvent was evaporated to dryness to afford 1-(5-methoxy-6-(5-methyl-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-ylamino)indolin-1-yl)ethanone (301 mg, 46.8 %) as a orange solid.
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