Selectfluor → HCID 59292824, Verbindung

HRID 2391926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2391926
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[CH:29][C:30]([C:37]2[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[C:39]([O:45][CH3:46])[CH:38]=2)=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:26])[CH3:23]>CC#N>[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[CH:29][C:30]([C:37]2[CH:38]=[C:39]([O:45][CH3:46])[CH:40]=[C:41]([O:43][CH3:44])[C:42]=2[F:21])=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:26])[CH3:23]

Komponenten

4

Edukt 2

HCID 2724933SelectfluorHCID 592928505-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

Produkt 1

HCID 59292824HCID 59292824, VerbindungAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

SelectFluor (2.04 g, 5.8 mmol, 2 equiv) was added to a cold (−5° C.) solution of 5-(3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 174.2) (970 mg, 2.9 mmol) in CH3CN (40 mL), under an argon atmosphere. The reaction mixture was allowed to warm to rt, stirred at that temperature for 6 h, quenched by addition of a saturated aqueous solution of NaHCO3, and concentrated. The residue was diluted in EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) followed by trituration in Et2O to provide 355 mg of the title compound: ESI-MS: 356.2 [M+H]+; tR=3.80 min (System 1); TLC: Rf=0.18 (Hex/EtOAc, 3:2).

Aufarbeitung

  1. customquenched by addition of a saturated aqueous solution of NaHCO3
  2. concentrationconcentrated
  3. additionThe residue was diluted in EtOAc
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-8001c32b469541cfa1dd47b226b262e6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273882B2

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