Reacción #71455

Ecuación de reacción

SelectFluor

8-(3,5-dimethoxyphenyl)-quinoxaline-5-carboxylic acid ethyl ester

NaHCO3

→

title compound

Rendimiento 46.8%

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

Rendimiento 46.8%

Disolventes

CH3CN

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to it over 6 h
2. 2
   OtroThe aqueous phase was separated
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe combined organic layers were washed with H2O and brine
5. 5
   Secadodried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Procedimiento

SelectFluor (105 mg, 0.30 mmol) was added to a cold (−5° C.) solution of 8-(3,5-dimethoxyphenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 115.1) (100 mg, 0.30 mmol) in CH3CN (2 mL), under an argon atmosphere. The reaction mixture was allowed to warm to it over 6 h and stirred at that temperature for additional 12 h and diluted in EtOAc and a saturated aqueous 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 50 mg of the title compound as an off-white solid. Title compound: ESI-MS: 357.2 [M+H]+; tR=4.58 min (System 1); TLC: Rf=0.24 (Hex/EtOAc, 3:2).

Fuente