Acetic Acid → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-methoxybenzoic acid

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To a solution of 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate C, 1.00 g, 4.36 mmol) in DMF (20 mL), was added 2-bromo-5-methoxybenzoic acid (1.01 g, 4.36 mmol), potassium carbonate (723 mg, 5.23 mmol), and copper (II) acetate (32 mg, 0.17 mmol). The mixture was stirred at 150° C. for 18 h and then cooled to rt. The solution was adjusted to pH 4 using glacial acetic acid. The mixture was extracted with dichloromethane (3×5 mL), and then the combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by HPLC (45-90% acetonitrile in water) to afford the product (500 mg, 33%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (s, 9H), 1.98 (s, 3H), 3.69 (s, 3H), 6.19 (s, 1H), 7.14 (dd, 1H), 7.26-7.37 (m, 6H), 9.49 (s, 1H), 13.25 (s, 1H); ES-MS m/z 380.3 (MH+); HPLC RT (min) 3.18.

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