Potassium Fluoride → N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-8-carboxamide

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Reaction Conditions

Reaction Steps

Potassium fluoride (725 mg, 12.5 mmol) was dried under vacuum and stirring, at 200° C. for 3 h. After cooling to room temperature, a solution of compound 101 (1.00 g, 2.32 mmol) in anhydrous dimethylsulfoxide (20 mL) was added. The mixture was then heated at 130° C., under argon, for 3 h. After cooling to room temperature, the solvent was evaporated under vacuum and the residue was chromatographed (Al2O3, AcOEt/cyclohexane, 9/1, v/v) to give compound 102 (821 mg, 1.98 mmol) as a yellow solid. Yield 85%; Rf (Al2O3, AcOEt/cyclohexane, 9/1, v/v) 0.42; mp 79-81° C.; IR (KBr) ν 1529, 1667, 2798, 2966, 3200-3300 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.04 (t, 6H, J=7.1 Hz), 2.59 (q, 4H, J=7.1 Hz), 2.70 (t, 2H, J=6.4 Hz), 3.61 (q, 2H, J=6.4 Hz), 7.15 (dd, 1H, 3JH-F=9.2 Hz, J=5.1 Hz), 8.53 (d, 1H, J=2.1 Hz), 8.83 (dd, 1H, 4JH-F=8.4 Hz, J=5.1 Hz), 9.05 (d, 1H, J=2.1 Hz), 11.04 (m, 1H); MS m/z 415 (M+, 1), 342 (1), 299 (4), 271 (1), 173 (2), 145 (6), 118 (2), 99 (8), 86 (100), 58 (9).

Provenance & Evidence