Reacción #71394

Ecuación de reacción

SelectFluor

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

→

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

Disolventes

CH3CN

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by addition of H2O
2. 2
   Concentraciónconcentrated
3. 3
   Otroto remove CH3CN
4. 4
   workup.ADDITIONThe resulting mixture was diluted with EtOAc/H2O
5. 5
   Filtraciónfiltered
6. 6
   Otroto provide a white solid (batch 1)
7. 7
   ExtracciónThe filtrate was extracted with EtOAc
8. 8
   LavadoThe organic phase was washed with H2O and brine
9. 9
   Secadodried (Na2SO4)
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated
12. 12
    Otroto afford batch 2
13. 13
    Otropurified by silica gel MPLC (Hex/EtOAc, 7:3)

Procedimiento

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).

Fuente