Aniline → 3-Phenylamino-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 2356895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356895
Br[C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:22]1([NH:21][C:2]2[C:3](=[O:20])[N:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:7]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 3

HCID 6115AnilineHCID 223190653-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-oneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 223191743-Phenylamino-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-oneAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

53 mg of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one and 23 mg of aniline were dissolved in 10 ml of toluene, to which 2 mg of palladium acetate, 7 mg of 1,1′-bis(diphenylphosphino)ferrocene and 23 mg of sodium tert-butoxide were added, and the mixture was stirred at 110° C. for a night. The reaction solution was cooled to room temperature, filtered by silica gel and washed with ether, and the filtrate was distilled under a vacuum to remove the solvent. The residue was refined by silica gel chromatography (NH silica) (hexane/ethyl acetate-based solvent), to obtain 47 mg of the subject compound.

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationfiltered by silica gel
  4. washwashed with ether
  5. distillationthe filtrate was distilled under a vacuum
  6. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-2fec551daf6e48ed8861d2f787e16023
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759367B2

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