4.1.18. 1-(3,4,5-Trimethoxybenzoyl)indoline-5-sulfonamide (4m)

This compound was prepared from 9 and 3,4,5-trimethoxybenzoyl chloride as described for 4a. A white powder, yield 58%, mp = 248–250 °C. HPLC (LW = 300 nm, gradient B 30/70/30% (35 min)) t_R = 10.9 min, purity 99%. ¹H NMR (400 MHz, DMSO-d₆): δ 7.85 (br s, 1H, Ar), 7.68 (s, 1H, Ar), 7.64 (d, J = 8.3 Hz, 1H, Ar), 7.24 (s, 2H, NH₂), 6.90 (s, 2H, Ar), 4.10 (t, J = 8.2 Hz, 2H, CH₂), 3.79 (s, 6H, 2OMe), 3.71 (s, 3H, OMe), 3.13 (t, J = 8.2 Hz, 2H, CH₂). ¹³C NMR (100 MHz, DMSO-d₆): δ 168.7, 153.3 (2C), 145.9, 139.5 (2C), 134.1, 132.2, 125.7, 122.9, 116.3, 105.1 (2C), 60.6, 56.6 (2C), 51.3, 27.8. HRMS (ESI) (m/z) [M+H]⁺: calculated for C₁₈H₂₁N₂O₆S 393.1115, found 333.1106. IR ν max, (film) cm⁻¹ 3336 s, 3189 m, 3079 w, 1644 s, 1592 m, 1566 w, 1539 w, 1482 s, 1433 m, 1394 s, 1333 s, 1315 s, 1257 m, 1194 s, 1169 m, 1152 s, 1111 w, 1079 s, 999 w, 912 s, 892 s, 869 s, 835 s, 802 s, 772 w, 741 w, 714 m, 683 w.