Acetic Acid → 5-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino]benzoic acid

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A mixture of 2-bromo-5-methoxy benzoic acid (1.31 g, 5.7 mmol), potassium carbonate (859 mg, 6.2 mmol), 5-amino-1-phenyl-pyrazole (900 mg, 5.7 mmol), and copper (II) acetate (21 mg, 0.11 mmol) in DMF (12 mL) was heated (150° C.) in a sealed tube for 16 h. After cooling, the reaction mixture was diluted with water (5 mL), and then acidified to pH 4 with acetic acid. The mixture was extracted with dichloromethane (3×10 mL), and then the combined organic extracts were washed with water (2×10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. HPLC purification of the residue (YMC propack C18 column, 150×20 mm ID, 30%-80% acetonitrile in water gradient) afforded 5-methoxy-2-[(1-phenyl-1H-pyrazol-5-yl)amino] benzoic acid (450 mg, 26%) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 13.33 (br s, 1H), 9.62 (br s, 1H), 7.64 (d, 1H), 7.34-7.58 (m, 6H), 7.00-7.11 (m, 2H), 6.30 (d, 1H), 3.69 (s, 3H); ES-MS m/z 310.1 (MH+); HPLC RT (min) 2.74.

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