[Synthesis]
To a 170 mL suspension of DME/EtOH/H2O (4:1:1) containing K2CO3 (4.65 g, 33.6 mmol), Pd(OAc)2 (0.189 g, 0.840 mmol), and PPh3 (0.882 g, 3.36 mmol), was added sequentially 2-nitrophenylboronic acid (3.37 g, 20.2 mmol) and 2-bromopyridine (1.60 mL, 16.8 mmol). The reaction mixture was stirred at 70 °C overnight and concentrated under reduced pressure. Water (100 mL) and Et2O (100 mL) were added to the concentrated residue and the aqueous layer was extracted with Et2O (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4 and the solvent evaporated. The residue was purified by silica gel column chromatography (eluent: hexane/EtOAc = 6:1) to afford 2-(2-nitrophenyl)pyridine (2.23 g, 66% yield) as a white solid. The spectral data of the product were in agreement with literature reports: rf = 0.28 (hexane/EtOAc = 2:1); 1H NMR (400 MHz, CDCl3): δ 8.66 (d, J = 5.0 Hz, 1H), 7.91 (d, J = 8.2 Hz, 1H), 7.81 (dd, J = 7.7, 7.7 Hz, 1H), 7.68 (d, J = 7.2 Hz, 1H), 7.63 (dd, J = 7.7, 7.7 Hz, 1H), 7.55 (dd, J = 7.7, 7.2 Hz, 1H), 7.48 (d, J = 8.2 Hz, 1H), 7.32 (dd, J = 7.7, 5.0 Hz, 1H). |