Water → HCID 117737274, compound

Participants

Reaction Steps

A RBF was charged with 5-(6-(benzylthio)-2-oxoquinolin-1(2H)-yl)-2-bromo-4-methoxybenzonitrile (798 mg, 1.672 mmol), acetonitrile (7867 μl), acetic acid (295 μl), and water (197 μl) to give a solution. The flask was cooled in an ice-water bath for 10 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (165 mg, 0.836 mmol) was added (0.5 equiv). After 10 min, an additional portion of 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (165 mg, 0.836 mmol) was added. After another 10 min, a final portion of 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (165 mg, 0.836 mmol) was added to the mixture. 2,3,4,5,6-pentafluorophenol (385 mg, 2.090 mmol) was added. After another minute, triethylamine (932 μl, 6.69 mmol) was added dropwise over 15 s. The mixture was stirred for 10 min then was diluted with water and EtOAc, and the layers were separated. The aq. layer was extracted with DCM (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was concentrated from EtOAc, then taken up in EtOAc and filtered. The collected solid was washed with EtOAc (3×), then dried under a stream of N2 (g) for 14 h to give perfluorophenyl 1-(4-bromo-5-cyano-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (566 mg, 0.941 mmol, 56.3% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) □=8.61 (d, J=2.3 Hz, 1 H), 8.27 (d, J=9.6 Hz, 1 H), 8.18 (s, 1H), 7.93 (dd, J=2.3, 9.0 Hz, 1 H), 7.88 (s, 1 H), 6.98 (d, J=9.0 Hz, 1 H), 6.90 (d, J=9.7 Hz, 1 H), 3.83 (s, 3 H). m/z (ESI) 601.0 (M+H)+.

Provenance & Evidence