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7-Acetyl-5-methylquinolin-8-yl trifluoromethanesulfonate → 1-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethanone

HRID 1192561
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1192561
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([CH3:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[F:23][C:24]1[CH:25]=[C:26]([Zn]I)[CH:27]=[CH:28][CH:29]=1>O1CCCC1>[F:23][C:24]1[CH:29]=[C:28]([C:7]2[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([CH3:17])=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:27]=[CH:26][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 583684117-Acetyl-5-methylquinolin-8-yl trifluoromethanesulfonateHCID 178505804HCID 178505804, Verbindung

Produkt 1

HCID 583686621-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethanoneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 7-acetyl-5-methylquinolin-8-yl trifluoromethanesulfonate (0.833 g, 2.50 mmol) in tetrahydrofuran (20 mL), with stirring, was added 0.5 M (3-fluorophenyl)(iodo)zinc in THF (10.0 mL, 5.0 mmol), followed by tetrahydrofurantetrakis(triphenylphosphine)palladium(0) (289 mg, 0.250 mmol). The reaction mixture was heated at 60° C. overnight, cooled to room temperature and quenched with sat. sodium bicarbonate. The mixture was filtered through a Celite pad. The filtrate was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The residue was purified on silica gel, eluting with 0 to 80% ethyl acetate in hexane, to give the desired product (0.379 g, 54%). LCMS calculated for C18H14FNO (M+H)+: m/z=280.1; Found: 280.0.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched with sat. sodium bicarbonate
  3. filtrationThe mixture was filtered through a Celite pad
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 80% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-b9deb54eb05a4b2c9bd0be7fc3704985
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680108B2

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