Sodium t-butoxide → 9-(9-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole

HRID 2039431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039431
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3[CH:23]=[CH:24][CH:25]=[N:26][C:15]2=3)[CH:2]=1.Br[C:28]1[CH:29]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]3[C:45]4[S:46][C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=5[C:44]=4[CH:43]=[CH:42][CH:41]=3)[CH:35]=2)[CH:31]=[CH:32][CH:33]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=C(C3C(OC)=CC=CC=3OC)C=CC=2)CCCCC1>[CH:43]1[C:44]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[S:46][C:45]=2[C:40]([C:36]2[CH:35]=[C:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([N:12]4[C:13]5[CH:1]=[CH:2][C:3]([N:14]6[C:22]7[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=7)[C:16]7[CH:23]=[CH:24][CH:25]=[N:26][C:15]6=7)=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH:29]=3)[CH:39]=[CH:38][CH:37]=2)=[CH:41][CH:42]=1

Komponenten

7

Edukt 3

HCID 23676156Sodium t-butoxideHCID 669744624-(3'-Bromobiphenyl-3-yl)dibenzothiopheneHCID 708151019-(9H-carbazol-3-yl)-pyrido[2,3-b]indole

Produkt 1

HCID 708151359-(9-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indoleAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphineKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A solution of 9-(9H-carbazol-3-yl)-pyrido[2,3-b]indole (2.50 g, 7.50 mmol), 4-(3′-bromo-[1,1′-biphenyl]-3-yl)dibenzo[b,d]thiophene (3.11 g, 7.50 mmol), Pd2(dba)3 (0.137 g, 0.150 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (0.123 g, 0.30 mmol), and sodium tert-butoxide (1.44 g, 15.00 mmol) in xylene (150 mL) was refluxed in nitrogen overnight. After cooling to room temperature, the reaction mixture was washed with water, dried over Na2SO4 and the solvent was evaporated. The residue was dissolved in hot toluene, mixed with celite, and purified by column chromatography with hexane:toluene (1:9 to 0:10, v/v) as eluent. The product was precipitated in ethanol, and further purified by thermal sublimation under vacuum (<105 torr) to yield 9-(9-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole as a white glassy solid (3.21 g).

Aufarbeitung

  1. washthe reaction mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in hot toluene
  5. additionmixed with celite
  6. custompurified by column chromatography with hexane:toluene (1:9 to 0:10
  7. customThe product was precipitated in ethanol
  8. customfurther purified by thermal sublimation under vacuum (<105 torr)

Quellen und Nachweise

ORD-Eintrag
ord-77d901fe3c9541b3b6d2a277e1de80e0
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580399B2

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