Ethanol → 7-acetyl-12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo [a,g]carbazole

HRID 530765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530765
[C:1]([N:4]1[C:16]2[C:11](=[CH:12][C:13](Br)=[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]3=2)[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]1=2)(=[O:3])[CH3:2].[C:26]1([N:32]2[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[N:34]=[C:33]2[C:41]2[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.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>[C:1]([N:4]1[C:16]2[C:11](=[CH:12][C:13]([C:44]3[CH:45]=[CH:46][C:41]([C:33]4[N:32]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=5[N:34]=4)=[CH:42][CH:43]=3)=[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]3=2)[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]1=2)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 532497794-(1-Phenyl-1H-benzimidazol-2-yl)phenylboronic AcidHCID 712778947-acetyl-12-bromo-7H-dibenzo [a,g]carbazole

Produkt 1

HCID 712782597-acetyl-12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo [a,g]carbazoleAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Following the above procedure, Suzuki coupling of 3.4 g of 7-acetyl-12-bromo-7H-dibenzo [a,g]carbazole and 3.8 g of 4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenylboronic acid were stirred together in 30 ml of toluene. To this was added 0.01 g of tetrakis(triphenylphosphine)palladium, 2.7 g of potassium carbonate and 10 ml of aqueous ethanol were added and refluxed under nitrogen for 6 h. The reaction was quenched with water and the toluene layer was removed and passed through a celite column. The organic layers were combined and then evaporated in a rotary evaporator under vacuum to yield 4.6 g of 7-acetyl-12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo [a,g]carbazole as a white solid.

Aufarbeitung

  1. additionwere added
  2. temperaturerefluxed under nitrogen for 6 h
  3. customThe reaction was quenched with water
  4. customthe toluene layer was removed
  5. customevaporated in a rotary evaporator under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6113bb22f8114640b99d78649f2a6266
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353085B2

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