2-Chloroaniline → N-(2-chlorophenyl)-1H-indazol-6-amine

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Palladium(II) acetate (0.342 g, 1.52 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.422 g, 2.28 mmol) were added to a stirred slurry of 2-chloroaniline (1.763 mL, 16.75 mmol), 6-bromo-1H-indazole (3 g, 15.23 mmol) and cesium carbonate (9.92 g, 30.45 mmol) in toluene (50 mL) at 23°C under nitrogen. The resulting slurry was stirred at 80 °C for 2 hours. The reaction was incomplete (both SM left) so the temperature was increased to 100°C and the reaction mixture was stirred for a further 2 hours. Mainly 2 SM detected. problem of solubility of bromoindazole? The reaction was incomplete and further Palladium(II) acetate (30mg), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (200mg) and cesium carbonate (1g) were added as well as dioxane and the slurry was stirred at 110 °C for a further 3 hours. Only SMs detected. No further work on this sample. Perform coupling with reverse coupling partners using Boc 6-aminoindazole. Known to work as used in project.

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