4-Chloro(1)benzothieno(3,2-d)pyrimidine → 4-(9'-phenyl-9H,9'H-[3,3'-bicarbazol]-9-yl)benzo[4,5]thieno[3,2-d]pyrimidine

HRID 634540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634540
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16]([C:20]4[CH:21]=[CH:22][C:23]5[NH:24][C:25]6[C:30]([C:31]=5[CH:32]=4)=[CH:29][CH:28]=[CH:27][CH:26]=6)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:34]1[C:35]2[S:42][C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[C:36]=2[N:37]=[CH:38][N:39]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.CC([O-])(C)C.[Na+]>C1(C)C=CC=C(C)C=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16]([C:20]4[CH:21]=[CH:22][C:23]5[N:24]([C:34]6[C:35]7[S:42][C:41]8[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=8[C:36]=7[N:37]=[CH:38][N:39]=6)[C:25]6[C:30]([C:31]=5[CH:32]=4)=[CH:29][CH:28]=[CH:27][CH:26]=6)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 8218354-Chloro(1)benzothieno(3,2-d)pyrimidineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolyl

Produkt 1

HCID 1178150564-(9'-phenyl-9H,9'H-[3,3'-bicarbazol]-9-yl)benzo[4,5]thieno[3,2-d]pyrimidineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 7929M-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

9-phenyl-9H,9′H-3,3′-bicarbazole (3.05 g, 7.47 mmol), 4-chlorobenzo[4,5]thieno[3,2-d]pyrimidine (1.812 g, 8.21 mmol), Pd2dba3 (0.342 g, 0.373 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (0.307 g, 0.747 mmol), and sodium 2-methylpropan-2-olate (1.794 g, 18.67 mmol) were charged to a 250 mL RBF, diluted in m-Xylene (Volume: 74.7 mL), degassed with nitrogen and heated to reflux at 150° C. overnight. The reaction was quenched with aqueous ammonium chloride and filtered through a plug of Celite® with dichloromethane (DCM). The crude was purified by column chromatography and then recrystallized from toluene/ethanol to give 4-(9′-phenyl-9H,9′H-[3,3′-bicarbazol]-9-yl)benzo[4,5]thieno[3,2-d]pyrimidine (1.95 g, 44% yield).

Aufarbeitung

  1. customdegassed with nitrogen
  2. temperatureheated
  3. customThe reaction was quenched with aqueous ammonium chloride
  4. filtrationfiltered through a plug of Celite® with dichloromethane (DCM)
  5. customThe crude was purified by column chromatography
  6. customrecrystallized from toluene/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4a1cbb43e1454b24a19bfa75b288a66b
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09324949B2

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