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

HRID 43116

Reaction equation

HRID 43116 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-da2b2ac714da47d188b017ca3a18f0a1
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

Loading…