Water → N-(2-nitropyridin-3-yl)pyridin-2-amine

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To a solution of 3-fluoro-2-nitropyridine (3.32 g, 23.38 mmol) and 2-aminopyridine (2.0 g, 21.25 mmol) in DMF (35.4 mL) was added potassium tert-butoxide (4.77 g, 42.5 mmol). The solution was stirred under nitrogen at rt overnight. After 22 h, the mixture was poured into water (100 mL) and extracted with EtOAc (2×100 mL). After drying with MgSO4, the solution was filtered and concentrated in vacuo to provide the crude material as a orange solid. The orange solid was purified by chromatography through a Redi-Sep™ pre-packed silica gel column (80 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide N-(2-nitropyridin-3-yl)pyridin-2-amine as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 9.53 (1H, s), 8.58 (1H, dd, J=8.4, 1.6 Hz), 8.15 (1H, dd, J=4.3, 1.4 Hz), 8.10-8.14 (1H, m), 7.66-7.76 (2H, m), 7.05 (1H, dt, J=8.4, 0.8 Hz), 6.93 (1H, ddd, J=7.2, 5.0, 0.9 Hz); LC-MS (ESI) m/z 217.0 [M+H]+.

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