Synthesis of Potent Indolin-2-one Derivative

Yellow powder (yield 39.2%); melt. pt. > 300 °C; ¹H NMR (700 MHz, DMSO-d₆) δ ppm: 2.08 (s, 3H, Acetamide Methyl), 3.24 (s, 3H, N-Methyl), 7.19 (s, 2H, Ar. Proton), 7.38–7.56 (m, 4.7H, Ar. Proton), 7.57–7.85 (m, 5H, Ar. Proton), 8.42 (s, 0.3H, Ar. Proton), 10.22, 10.25 (2s, 1H, Acetamide NH), 14.27 (s, 1H, Hydrazide NH); ¹³C NMR (176 MHz, DMSO-d₆) δ ppm: 24.55 (Acetamide Methyl), 26.22 (N-Methyl), 110.48, 117.17 (d, ²J_CF = 23.3 Hz), 119.07, 119.53, 121.06, 121.31, 123.73, 127.36, 128.98 (d, ³J_CF = 9.5 Hz), 129.99, 130.31, 132.42, 134.34, 138.56, 141.86, 144.51, 154.83, 155.74 (Hydrazide Carbonyl), 161.33 (Indolin-2-one Carbonyl), 169.33 (Acetamide Carbonyl); anal. calcd. for C₂₆H₂₀FN₇O₃ (497.49 g/mol): C, 62.77; H, 4.05; N, 19.71; practical C, 62.62; H, 4.07; N, 19.79; HRMS (ESI) for C₂₆H₂₁FN₇O₃, calcd 498.1684, found 498.1691 [M+H]⁺, and for C₂₆H₂₀FN₇NaO₃, calcd 520.1504, found 520.1511 [M+Na]⁺.