Aniline → 2,6-dichloro-N-phenylpyridin-3-amine

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BINAP (4.67 mg, 7.50 µmol) and Pd2dba3 (2.289 mg, 2.50 µmol) were dissolved in dioxane (1ml) and flushed with nitrogen. 3-bromo-2,6-dichloropyridine (0.023 g, 0.1 mmol), aniline (0.018 mL, 0.20 mmol) and sodium tert-butoxide (0.014 g, 0.15 mmol) were weight in another flask and flushed with nitrogen. The ligand- Pd mixture was subjoined and the reaction mixture was stirred at 100°C over night. Detection of the reaction was done by LC/MS. LC/MS showed the completion of the reation. the 3-bromo-2,6-dichloropyridine as well as the aniline were gone, but no desired product was detected. NMR verified the observations. The products have not been identified.

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