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

HRID 1957900ノート

反応式

HRID 1957900 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-734cbe2005514f718471752ad99bebab
出典データセット
uspto-grants-2013_04
特許番号
US08409729B2

反応ノート

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