Dimethylformamide → 4-[(E)-2-(4-fluorophenyl)vinyl]-2-(4-methoxybenzyloxy)-pyridine

HRID 15050

Reaktionsgleichung

[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.I[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[CH:23]=1>[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:7]/[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[CH:23]=2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

4-Fluorostyrene (3.0 mL), dichlorobis(triphenylphosphine)palladium (870 mg) and potassium carbonate (5.2 g) were added to DMF (70 mL) solution of 4-iodo-2-(4-methoxybenzyloxy)pyridine (4.25 g) and stirred at 100° C. for 19 hours. Saturated brine was added to the reaction liquid, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19-1:9-1:4) to provide the title compound (2.55 g, 61%).

Aufarbeitung

extractionfollowed by extraction with ethyl acetate
dry with materialdrying over anhydrous magnesium sulfate
concentrationConcentrating the solvent under reduced pressure
customthe resulting residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19-1:9-1:4)

Quellen und Nachweise

ORD-Eintrag: ord-59420ad30a3644888fc89d1d064672b1
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732456B2

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