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

HRID 1957900노트

반응식

HRID 1957900 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-734cbe2005514f718471752ad99bebab
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08409729B2

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