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

HRID 1957900Notes

Reaction equation

HRID 1957900 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-734cbe2005514f718471752ad99bebab
Source dataset
uspto-grants-2013_04
Patent number
US08409729B2

Reaction notes

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