Acetonitrile → 5-(2-Formylphenyl)picolinonitrile

HRID 1988024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988024
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)O1.Br[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[O:22].C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>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.C(OCC)(=O)C>[CH:21]([C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=1)=[O:22]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 164141882-Cyanopyridine-5-boronic acid pinacol ester

Produkt 1

HCID 866210895-(2-Formylphenyl)picolinonitrileAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a microwave vial, 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carbonitrile (279 mg, 1.51 mmol), 2-bromo-benzaldehyde (230 mg, 1 mmol) and 2 ml of actonitrile were mixed. Then, 2 ml of 1N aqueous sodium carbonate was added, followed by 5 mole percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 100° C. for 10 minutes with microwave irradiation. After cooling, 50 ml of ethyl acetate was added, the organic layer was separated, washed with water and dried over sodium sulfate. The organic solvent was evaporated to give crude product which was purified by ISCO to give 150 mg of 5-(2-formyl-phenyl)-pyridine-2-carbonitrile, yield 72%.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe organic solvent was evaporated
  7. customto give crude product which
  8. customwas purified by ISCO

Quellen und Nachweise

ORD-Eintrag
ord-00236c3c2a8f4e388a830ecd6c384936
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553840B2

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