N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → N-[2-[N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide

Participants

Reaction Steps

This compound was prepared, starting from compound 59 (600 mg, 2.36 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2C2/EtOH, 99/1, v/v) to give compound 60 (902 mg, 1.68 mmol) as a light sensitive brown oil. Yield 71%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.46; IR (CCl4) ν 1117, 1289, 1526, 1549, 1683, 2800-3000, 3410 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.08 (t, 3H, J=7.1 Hz), 2.70 (q, 2H, J=7.1 Hz), 2.83 (t, 2H, J=6.1 Hz), 2.99 (t, 2H, J=5.3 Hz), 3.57 (q, 2H, J=6.1 Hz), 4.17 (t, 2H, J=5.3 Hz), 7.36 (dd, 1H, J=4.2, 8.4 Hz), 7.43 (dd, 1H, J=1.7, 8.4 Hz), 7.61 (d, 1H, J=8.8 Hz), 7.94 (dd, 1H, J=1.7, 4.2 Hz), 7.99 (dd, 1H, J=1.8, 8.8 Hz), 8.29 (m, 1H), 8.53 (d, 1H, J=1.8 Hz), 9.57 (s, 1H); ESI-MS m/z 536.9 [M+H]+.

Provenance & Evidence