2-Bromopyridine → 1-(5-Fluoro-2,3'-bipyridin-6'-yl)ethanone

HRID 216328

Reaktionsgleichung

Reaktionsgleichung von HRID 216328
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[N:13][CH:14]=1.C[Sn](C)C.C[Sn](C)C.[F-:26].[K+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:26][C:5]1[CH:6]=[CH:7][C:2]([C:9]2[CH:14]=[N:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 79732-BromopyridineHCID 522689Potassium FluorideHCID 6327618HexamethylditinHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Produkt 1

HCID 591620141-(5-Fluoro-2,3'-bipyridin-6'-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Palladium tetrakis(triphenylphosphine) (289 mg, 0.25 mmol) was added to a degassed, ambient temperature solution of 2-bromopyridine (660 mg, 3.75 mmol), 1-(5-bromo-pyridin-2-yl)-ethanone (500 mg, 2.5 mmol) and hexamethylditin (1.2 g, 3.75 mmol) in degassed 1,4-dioxane (8 mL). After stirring at 110° C. overnight, the reaction mixture was cooled and KF/celite (1:1) was added. After stirring vigorously for 1 hr, reaction mixture was filtered and concentrated. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded the title compound.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. stirringAfter stirring vigorously for 1 hr
  3. customreaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-43d217c3562947fcb3f9a7548c588cb2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

Verknüpfte Notizen

Wird geladen…