4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-2-carboxamide → N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-2-carboxamide

Participants

Reaction Steps

This compound was prepared, starting from compound 105 (1.00 g, 2.32 mmol), according to the procedure developed for compound 102. Reaction time at 200° C.: 2 h, reaction time at 140° C.: 5 h; the purification was performed using column chromagraphie (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 106 (458 mg, 1.10 mmol) as a yellow solid. Yield 48%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.42; mp 58-60° C.; IR (KBr) ν 1342, 1486, 1518, 1555, 1681, 2760, 2966, 3385 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.06 (t, 6H, J=7.1 Hz), 2.56 (q, 4H, J=7.1 Hz), 2.69 (t, 2H, J=6.1 Hz), 3.54 (q, 2H, J=6.1 Hz), 7.76 (dd, 1H, 5JH-F=1.2 Hz, J=8.9 Hz), 7.96 (m, 2H), 8.42 (d, 1H, J=1.7 Hz), 8.50 (m, 1H); ESI-MS m/z 415.9 [M+H]+.

Provenance & Evidence