Selectfluor → 5-Bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline

HRID 2409679Notes

Reaction equation

HRID 2409679 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[Br:22][C:23]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[C:35]([O:41][CH3:42])[CH:34]=2)=[C:29]2[C:24]=1[N:25]=[CH:26][CH:27]=[N:28]2>CC#N>[Br:22][C:23]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[C:35]([O:41][CH3:42])[C:34]=2[F:21])=[C:29]2[C:24]=1[N:25]=[CH:26][CH:27]=[N:28]2

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 592928255-Bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline

Product 1

HCID 592929615-Bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. customquenched by addition of H2O
  2. concentrationconcentrated
  3. customto remove CH3CN
  4. additionThe resulting mixture was diluted with EtOAc/H2O
  5. filtrationfiltered
  6. customto provide a white solid (batch 1)
  7. extractionThe filtrate was extracted with EtOAc
  8. washThe organic phase was washed with H2O and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto afford batch 2
  13. custompurified by silica gel MPLC (Hex/EtOAc, 7:3)

Sources & evidence

ORD record
ord-2fbdd33fcc28492e9dc276e4bc9556ee
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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