Triphenylphosphine → 5-(1-Methoxyimino-indan-5-yl)-4-pyridin-4-yl-furan-2-carbaldehyde

HRID 271515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271515
Br[C:2]1[CH:3]=[C:4]([CH:19]=[O:20])[O:5][C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[N:16][O:17][CH3:18])[CH2:11][CH2:10]2.C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][N:16]=[C:12]1[C:13]2[C:9](=[CH:8][C:7]([C:6]3[O:5][C:4]([CH:19]=[O:20])=[CH:3][C:2]=3[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 867607594-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehyde

Produkt 1

HCID 867607605-(1-Methoxyimino-indan-5-yl)-4-pyridin-4-yl-furan-2-carbaldehydeAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A degassed mixture of the product of Step 4 (2.0 g, 6.0 mmol) and 4-tributylstannylpyridine (2.5 g, 6.8 mmol) in toluene (100 ml) was treated with triphenylphosphine (156 mg, 0.6 mmol) and palladium acetate (67 mg, 0.3 mmol) then heated under reflux for 60 hours. The reaction mixture was concentrated in vacuo and the product purified by silica gel chromatography eluting with ethyl acetate/hexane (1:1) and then ethyl acetate to give the title compound (1.37 g, 69%); MS(ES+) m/e 333 [M+H]+.

Aufarbeitung

  1. temperaturethen heated
  2. temperatureunder reflux for 60 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe product purified by silica gel chromatography
  5. washeluting with ethyl acetate/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d59478a4e454451788f17817b8af18ac
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452906B2

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