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

HRID 43116

反応式

HRID 43116 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-da2b2ac714da47d188b017ca3a18f0a1
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

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