Acetic Acid → 2-{[3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate D, 100 mg, 0.37 mmol) in DMF (3 mL), was added 2-iodobenzoic acid (93 mg, 0.37 mmol), potassium carbonate (62 mg, 0.45 mmol), and copper (II) acetate (3 mg, 0.01 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 title compound (17 mg, 12%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 2.08 (s, 3H), 6.85 (ddd, 1H), 6.93 (s, 1H), 7.24 (ddd, 2H), 7.42 (m, 6H), 7.84 (dd, 1H), 7.92 (ddd, 2H), 10.02 (s, 1H), 13.23 (s, 1H); ES-MS m/z 388.2 (MH+); HPLC RT (min) 3.47.

Provenance & Evidence