Reaktion #71457

Reaktionsgleichung

Sulfuryl chloride

8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester

→

title compound

Ausbeute 82.7%

8-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester

Ausbeute 82.7%

Lösungsmittel

CH3CN

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched by addition of a saturated solution of NaHCO3
2. 2
   Temperaturto warm to it
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONThe residue was diluted in EtOAc
5. 5
   SonstigeThe aqueous phase was separated
6. 6
   Extraktionextracted with EtOAc
7. 7
   WaschenThe combined organic layers were washed with H2O and brine
8. 8
   Trocknendried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Vorschrift

Sulfuryl chloride (0.35 mL, 4.33 mmol, 1.1 equiv) in CH3CN (10 mL) was added dropwise to a cold (−30° C.) solution of 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 143.1) (1.4 g, 3.93 mmol) in CH3CN (40 mL). The reaction mixture was quenched by addition of a saturated solution of NaHCO3, allowed to warm to it and concentrated. The residue was diluted in EtOAc and a saturated solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 1.27 g of the title compound as a white solid. Title compound: ESI-MS: 391.1 [M+H]+; tR=4.71 min (System 1); TLC: Rf=0.12 (Hex/EtOAc, 3:2).

Quelle