Potassium Fluoride → N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-3-carboxamide

HRID 2273662Notes

Reaction equation

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

Participants

Conditions

Temperature: 200 °C

Procedure

Potassium fluoride (674 mg, 11.6 mmol) was dried under vacuum and stirring, at 200° C. for 3 h. After cooling to room temperature, a solution of compound 95 (1.00 g, 2.32 mmol) in anhydrous N,N-dimethylformamide (20 mL) was added. The mixture was then heated at 130° C., under argon, for 2 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 96 (0.50 g, 1.20 mmol) as a yellow solid. Yield 52%; Rf (Al2O3, AcOEt/cyclohexane, 9/1, v/v) 0.46; mp 88-90° C.; IR (KBr) ν 1105, 1342, 1518, 1656, 2830, 2966, 3405 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.07 (t, 6H, J=7.1 Hz), 2.59 (q, 4H, J=7.1 Hz), 2.69 (t, 2H, J=5.9 Hz), 3.57 (q, 2H, J=5.9 Hz), 7.58 (se, 1H), 7.86 (d, 1H, J=9.0 Hz), 8.06 (dd, 1H, J=1.8, 9.0 Hz), 8.54 (d, 1H, J=1.8 Hz), 9.44 (d, 1H, 4JH-F=10.6 Hz); MS m/z 415 (M+, 1), 299 (3), 145 (1), 118 (3), 86 (100), 58 (9).

Workup

temperatureAfter cooling to room temperature
temperatureThe mixture was then heated at 130° C., under argon, for 2 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-e208b036f5ac4ac2844d978d0cb5a02c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09125937B2

Reaction notes

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