Potassium Phosphate, Tribasic → 1-(3-(3'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazol-9-yl)ethanone

HRID 1957900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957900
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:21](=[O:23])[CH3:22])[C:13]4[C:18]([C:19]=3[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[C:34]([N:38]3[C:50]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[C:44]4[C:39]3=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:35]=[CH:36][CH:37]=2)O1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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]>[CH:40]1[C:39]2[N:38]([C:34]3[CH:33]=[C:32]([C:2]4[CH:7]=[CH:6][CH:5]=[C:4]([C:8]5[CH:9]=[CH:10][C:11]6[N:12]([C:21](=[O:23])[CH3:22])[C:13]7[C:18]([C:19]=6[CH:20]=5)=[CH:17][CH:16]=[CH:15][CH:14]=7)[CH:3]=4)[CH:37]=[CH:36][CH:35]=3)[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44]=2[CH:43]=[CH:42][CH:41]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 586908999-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazoleHCID 712363961-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone

Produkt 1

HCID 712364021-(3-(3'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazol-9-yl)ethanoneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture solution of 1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone (2.50 g, 6.86 mmol), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (2.53 g, 6.86 mmol), Pd2(dba)3 (0.063 g, 0.069 mmol), (SPhos) (0.056 g, 0.137 mmol) and K3PO4 (4.74 g, 20.59 mmol) in toluene (180 mL) and water (5 mL) was refluxed under N2 overnight. After cooling to room temperature, the organic solution was isolated. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (1/1 to 1/4, v/v) as eluent to yield 1-(3-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-9H-carbazol-9-yl)ethanone (3.2 g, 89%) as a white solid.

Aufarbeitung

  1. customthe organic solution was isolated
  2. customUpon evaporation of the solvent
  3. customthe residue was purified by column chromatography on silica gel with hexane/DCM (1/1 to 1/4, v/v) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-734cbe2005514f718471752ad99bebab
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08409729B2

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