2-Aminobiphenyl → N-[1,1'-Biphenyl]-2-YL-4-dibenzofuranamine

HRID 929274

Reaktionsgleichung

Reaktionsgleichung von HRID 929274
C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:19](OC)=[CH:18][CH:17]=[CH:16][C:15]=2[O:22]C)CCCCC1.[C:30]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1.IC1C2OC3C=CC=CC=3C=2C=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:30]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:16]1[C:15]2[O:22][C:10]3[CH:11]=[CH:12][CH:13]=[CH:8][C:9]=3[C:14]=2[CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 70152-AminobiphenylHCID 4582574-IododibenzofuranHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 68904161N-[1,1'-Biphenyl]-2-YL-4-dibenzofuranamineAusbeute 837,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

Toluene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.7 g, 4.2 mmol), and Pd2(dba)3 (1.0 g, 1.1 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (3.4 g, 20.0 mmol), 4-iododibenzo[b,d]furan (10.3 g, 35.0 mmol), and sodium tert-butoxide (6.7 g, 70.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 24 h. After cooling, the reaction mixture was filtered through a silica pad and washed with DCM. The solvent was removed in vacuo and the residue was purified by flash chromatography using 25% DCM/hexane (containing 0.75% triethylamine) to yield N-([1,1′-biphenyl]-2-yl)dibenzo[b,d]furan-4-amine (11.8 g, 98% yield) as a colorless oil.

Aufarbeitung

  1. customToluene (250 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 24 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with DCM
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a43bcae1d0cb4982a89c74011ebd7937
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09293712B2

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