Sodium Carbonate → 4-[2-(4-Fluorophenyl)ethyl]-2-(4-methoxybenzyloxy)-pyridine

HRID 15056

Reaktionsgleichung

Reaktionsgleichung von HRID 15056
[CH:1]12B[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3]C2.FC1C=CC(C=C)=CC=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][N:31](C3C=CC(OCCN4CCCC4)=CC=3)[C:30](=[O:48])[CH:29]=2)=[CH:22][CH:21]=1.[C:49](=O)([O-])[O-:50].[Na+].[Na+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.C1COCC1>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[C:30]([O:48][CH2:1][C:8]3[CH:3]=[CH:4][C:5]([O:50][CH3:49])=[CH:6][CH:7]=3)[CH:29]=2)=[CH:24][CH:25]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 678834-FluorostyreneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 111888914-[(e)-2-(4-Fluorophenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1h-pyridin-2-one

Produkt 1

HCID 684311084-[2-(4-Fluorophenyl)ethyl]-2-(4-methoxybenzyloxy)-pyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

9-Borabicyclo[3.3.1]nonane (540 mg) was added to THF solution (5 mL) of 4-fluorostyrene (240 mL) and stirred at room temperature for 2 hours. To the reaction liquid, the compound synthesized in Step (1) of Example 45(340 mg), tetrakis(triphenylphosphine)palladium (60 mg), DMF (5 mL) and 2M aqueous sodium carbonate solution (1 mL) were added 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 residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4) to provide the title compound (336 mg, 100%).

Aufarbeitung

  1. customTo the reaction liquid
  2. stirringstirred at 100° C. for 19 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. concentrationConcentrating the solvent under reduced pressure
  6. customthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4)

Quellen und Nachweise

ORD-Eintrag
ord-176101cd28c147d0814db60ad04c21e6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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