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. pyridin-3-amine (3.57 g, 37.98 mmol) was dissolved in DME (10 mL). To the mixture was added 10 mL of stock solution, and sodium tert-butoxide (4.26 g, 44.30 mmol). 5 min later, to the mixtue was added a solution of 3-bromopyridine (3.05 mL, 31.65 mmol) in DME (10 mL). The mixture was heated at 100 °C overnight. LCMS1 showed the result after 1 h heating. LCMS2 showed the result after 18 h heating, which showed the product formation, and the starting material 3-BrPy. LCMS3 showed the result after 40 h heating. LCMS4 was after 60h. To the mixture was added 50 mL DCM and acetic acid (2 mL, 34.94 mmol). The mixture was stirred for 10 min, and then 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 0-60% acetonitrile in H2O/ACN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. The compounds were detected by UV at 254nm (LCMS5). After freezing-dried overnight, product dipyridin-3-ylamine (0.540 g, 9.97 %) was obtained.

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