3-Aminopyridine → N-pyridin-3-ylpyridin-3-amine

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Stock solution: 2.43 M solution of CyPF-tBu/Pd(OAc)2 (1:1) in DME. 3-bromopyridine (0.482 mL, 5.00 mmol) was dissolved in DME (10 mL). To the solution was added 2mL of stock solution, and sodium tert-butoxide (0.673 g, 7.00 mmol). To the mixture was added a solution of pyridin-3-amine (0.565 g, 6.00 mmol) in DME (10 mL). The mixture was heated at 90 °C overnight. LCMS showed the product formation, but the starting material 3-BrPy was still . To the mixture was added 2 mL stock solution additionally, and the mixture was heated at 90 °C for another 2h, but LCMS did not show improvement. The mixture was filtered. The filtrate was concentrated, and the compound was purified by preparative HPLC on a XBridge C18 column (10 µm 250x50 ID mm) using a gradient of 0-50% acetonitrile in H2O/ACN/NH3 95/5/0.2 buffer over 15 minutes with a flow of 100 mL/min. The compounds were detected by UV at 254nm. To the fractions (ca. 60mL) were added 5 mL of HOAc. The product was freezing-dried to give the product dipyridin-3-ylamine (0.031 g, 3.62 %).

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