N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-8-iodo-[1,6]naphthyridine-2-carboxamide

Participants

Reaction Steps

This compound was prepared, starting from compound 5 (100 mg, 0.44 mmol) and ethyl 8-iodo-[1,6]naphthyridine-2-carboxylate (72) (102 mg, 0.31 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 73 (151 mg, 0.30 mmol) as a yellow oil. Yield 96%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.65; IR (CCl4) ν 1467, 1518, 1685, 2700-3000 cm−: 1H NMR (200 MHz, CDCl3) δ 1.10 (t, 3H, J=7.1 Hz), 2.71 (q, 2H, J=7.1 Hz), 2.83 (t, 2H, J=6.0 Hz), 2.97 (t, 2H, J=5.6 Hz), 3.59 (q, 2H, J=6.0 Hz), 4.12 (t, 2H, J=5.6 Hz), 6.82 (ddd, 1H, 5JH-F=0.5 Hz, J=4.8, 7.9 Hz), 7.12 (ddd, 1H, 4JH-F=10.1 Hz, J=1.6, 7.9 Hz), 7.43 (td, 1H, 4JH-F=1.6 Hz, J=1.6, 4.8 Hz), 8.32 (d, 1H, J=8.4 Hz), 8.40 (d, 1H, J=8.4 Hz), 8.79 (m, 1H), 9.10 (s, 1H), 9.13 (s, 1H); ESI-MS m/z 509.9 [M+H]+.

Provenance & Evidence