反応 #71457

反応方程式

Sulfuryl chloride

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

→

title compound

収率 82.7%

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

収率 82.7%

溶媒

CH3CN

CH3CN

反応条件

後処理

1. 1
   その他The reaction mixture was quenched by addition of a saturated solution of NaHCO3
2. 2
   温度to warm to it
3. 3
   濃縮concentrated
4. 4
   workup.ADDITIONThe residue was diluted in EtOAc
5. 5
   その他The aqueous phase was separated
6. 6
   抽出extracted with EtOAc
7. 7
   洗浄The combined organic layers were washed with H2O and brine
8. 8
   乾燥dried (Na2SO4)
9. 9
   ろ過filtered
10. 10
    濃縮concentrated
11. 11
    その他The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

実験手順

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).

出典