Reaction Steps
This compound was prepared, starting from compound 5 (200 mg, 0.88 mmol) and ethyl 6-iodoquinoline-2-carboxylate (66) (203 mg, 0.62 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, 98/2, v/v) to give compound 67 (302 mg, 0.59 mmol) as a brown oil. Yield 96%; Rf (Al2O3, CH2Cl2/EtOH, 98/2, v/v) 0.68; IR (CCl4) ν 1190, 1466, 1522, 1683, 2960 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.13 (t, 3H, J=7.1 Hz), 2.76 (q, 2H, J=7.1 Hz), 2.87 (t, 2H, J=6.0 Hz), 3.02 (t, 2H, J=5.8 Hz), 3.62 (q, 2H, J=6.0 Hz), 4.14 (t, 2H, J=5.8 Hz), 6.95 (ddd, 1H, 5JH-F=0.7 Hz, J=4.8, 7.8 Hz), 7.21 (ddd, 1H, 4JH-F=10.0 Hz, J=1.5, 7.8 Hz), 7.65 (m, 1H), 7.66 (d, 1H, J=8.9 Hz), 7.94 (dd, 1H, J=1.9, 8.9 Hz), 8.16 (d, 1H, J=8.6 Hz), 8.26 (s, 1H), 8.29 (d, 1H, J=8.6 Hz), 8.57 (m, 1H): ESI-MS m/z 508.9 [M+H]+.
