Water → HCID 58958618, compound

Participants

Reaction Steps

To a solution of 5-methyl-2-{[1-(2-methylphenyl)-3-(4-methylphenyl)-1H-pyrazol-5-yl]amino}benzoic acid (Example 65), (49.5 mg, 0.13 mmol) in AcOH/DCM (1:1, v/v) (2 mL) was added a solution of NIS (28 mg, 0.13 mmol) in DCM (1 mL). The reaction was stirred at rt for 3 h. Water (1 mL) was added to the reaction mixture. The water layer was extracted with DCM (2 mL), and the combined organic layers were washed with sodium sulfite and brine, and concentrated under reduced pressure. The crude product was subjected to HPLC purification with a gradient elution from 30% to 95% acetonitrile in water to afford 9.1 mg (14%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 8.88 (s, 1H), 7.85 (d, 2H), 7.74 (s, 1H), 7.18-7.32 (m, 7H), 6.58 (d, 1H), 2.41 (s, 3H), 2.25 (s, 3H), 2.21 (s, 3H). ES-MS m/z 524.1 (MH+); HPLC RT (min) 4.35.

Provenance & Evidence