反应 #71394

反应方程式

SelectFluor

5-bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline

→

5-bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline

溶剂

CH3CN

反应条件

后处理

1. 1
   其他quenched by addition of H2O
2. 2
   浓缩concentrated
3. 3
   其他to remove CH3CN
4. 4
   workup.ADDITIONThe resulting mixture was diluted with EtOAc/H2O
5. 5
   过滤filtered
6. 6
   其他to provide a white solid (batch 1)
7. 7
   萃取The filtrate was extracted with EtOAc
8. 8
   洗涤The organic phase was washed with H2O and brine
9. 9
   干燥dried (Na2SO4)
10. 10
    过滤filtered
11. 11
    浓缩concentrated
12. 12
    其他to afford batch 2
13. 13
    其他purified by silica gel MPLC (Hex/EtOAc, 7:3)

实验过程

SelectFluor (20.5 g, 58 mmol, 2 equiv) was added portionwise to a solution of 5-bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline (Step 1.4) (10 g, 29 mmol) in CH3CN (300 mL) at rt. The reaction mixture was stirred at rt for 0.5 h, quenched by addition of H2O and concentrated to remove CH3CN. The resulting mixture was diluted with EtOAc/H2O and filtered to provide a white solid (batch 1). The filtrate was extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to afford batch 2. The two batches were combined and purified by silica gel MPLC (Hex/EtOAc, 7:3) to afford a sample of 5-bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline (Step 94.3) and a sample of the title compound which was further purified by trituration in EtOAc to provide 2.28 g of a white solid. Title compound: ESI-MS: 381.0/382.9 [M+H]+; tR=4.92 min (System 1); TLC: Rf=0.26 (Hex/EtOAc, 7:3).

来源