To a solution of 2-amino-3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.163 g, 0.51 mmol) in ethylene glycol dimethylether (5 mL) was added N-(methyl-2-pyridinyl)-6-methyl-4-trifluoromethylsulfonyloxy-2-pyridone (0.136 g, 0.41 mmol), bis(triphenylphoshine)palladium (II) dichloride (0.029 g, 0.04 mmol), and sodium carbonate (0.62 mL, 1.24 mmol of 2M). The resulting mixture was heated at reflux for 3 hours. After cooling and concentration in vacuo the resulting dark solid was purified (SiO2, 50% ethyl acetate/methylene chloride to 3% methanol in 50% ethyl acetate/methylene chloride) to provide the title compound as an orange solid (0.176 g, 89%). 1H NMR (500 MHz, CDCl3) δ 2.41 (s, 3H), 3.39 (s, 3H), 5.5 (s, 2H), 6.28 (s, 1H), 6.68 (s, 1H), 7.3-7.1 (m, 2H), 7.62 (t, 1H), 8.49 (s, 1H), 8.61 (s, 1H).
