2-(Tributylstannyl)pyridine → 4-(3-Bromo-furan-2-yl)-pyridine

HRID 1593422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593422
C([Sn]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)(CCCC)CCCC)CCC.Br[C:21]1[O:22][CH:23]=[CH:24][C:25]=1[Br:26]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:26][C:25]1[CH:24]=[CH:23][O:22][C:21]=1[C:18]1[CH:19]=[CH:14][N:15]=[CH:16][CH:17]=1

Komponenten

6

Edukt 2

HCID 6077842-(Tributylstannyl)pyridineHCID 70215012,3-Dibromofuran

Produkt 1

HCID 157218314-(3-Bromo-furan-2-yl)-pyridineAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of tributylstannylpyridine (8.0 g, 21.7 mmol) and 2,3-dibromofuran (5.9 g, 26.1 mmol) in dry toluene (200 ml) was treated with bis(triphenylphosphine)palladium (II) chloride (1.5 g, 2.2 mmol) and heated at 100° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to afford the title compound (1.2 g, 25%); 1H NMR (CDCl3) 8.66 (2H, d, J 11 Hz), 7.84 (2H, d, J 11 Hz), 7.50 (1H, d, J 3 Hz), 6.60 (1H, d, J 3 Hz).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-de1c0fa68a7a4d31b1479e821a53b612
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297694B2

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