Reacción #1591656

Ecuación de reacción

2,3,4,5,6-pentafluorophenol

6-(benzylthio)-1-(4-bromo-2-methoxyphenyl)quinolin-2(1H)-one

water

water

1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione

Triethylamine

1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione

→

Perfluorophenyl 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

Rendimiento 72.6%

Disolventes

acetic acid

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a solution
2. 2
   TemperaturaThe flask was cooled in an ice-water bath for 10 min
3. 3
   workup.WAITAfter another 20 min
4. 4
   workup.STIRRINGthe mixture was stirred for 20 min
5. 5
   Extracciónextracted with DCM (3×)
6. 6
   SecadoThe combined organic extracts were dried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel loading column, 10-60% EtOAc/Heptane)

Procedimiento

A RBF was charged with 6-(benzylthio)-1-(4-bromo-2-methoxyphenyl)quinolin-2(1H)-one (1.777 g, 3.93 mmol), acetonitrile (18.49 ml), acetic acid (0.693 ml), and water (0.462 ml) 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 (0.813 g, 4.12 mmol) was added in one portion. After 20 min, an additional portion of 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.813 g, 4.12 mmol) was added in one portion. After another 20 min, 2,3,4,5,6-pentafluorophenol (1.085 g, 5.89 mmol) was added, and the mixture was stirred for 5 min. Triethylamine (2.190 ml, 15.71 mmol) was added dropwise over 30 s then the mixture was stirred for 20 min. The reaction mixture was diluted with water and extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel loading column, 10-60% EtOAc/Heptane). Perfluorophenyl 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (1.644 g, 2.85 mmol, 72.6% yield) was isolated as a white foam. 1H NMR (400 MHz, DMSO-d6) □=8.59 (d, J=2.2 Hz, 1H), 8.24 (d, J=9.6 Hz, 1 H), 7.95 (dd, J=2.3, 9.1 Hz, 1 H), 7.56 (d, J=1.9 Hz, 1 H), 7.44-7.26 (m, 2 H), 6.86 (dd, J=9.4, 13.7 Hz, 2 H), 3.72 (s, 3 H). m/z (ESI) 575.9 (M+H)+.

Fuente