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

HRID 2273666Notes

Reaction equation

[F-:1].[K+].Cl[C:4]1[C:13]2[C:8](=[C:9]([C:15]([NH:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:16])[CH:10]=[C:11]([I:14])[CH:12]=2)[N:7]=[CH:6][CH:5]=1>CS(C)=O>[CH2:21]([N:20]([CH2:23][CH3:24])[CH2:19][CH2:18][NH:17][C:15]([C:9]1[CH:10]=[C:11]([I:14])[CH:12]=[C:13]2[C:8]=1[N:7]=[CH:6][CH:5]=[C:4]2[F:1])=[O:16])[CH3:22]

Participants

Conditions

Temperature: 200 °C

Procedure

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).

Workup

temperatureAfter cooling to room temperature
temperatureThe mixture was then heated at 130° C., under argon, for 3 h
temperatureAfter cooling to room temperature
customthe solvent was evaporated under vacuum
customthe residue was chromatographed (Al2O3, AcOEt/cyclohexane, 9/1

Sources & evidence

ORD record: ord-8748009bc260499ab4191702f4b56820
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09125937B2

Reaction notes

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