9-Acetyl-3-bromocarbazole → 1-(3-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)ethanone

HRID 403150노트

반응식

HRID 403150 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15](=[O:17])[CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]([N:32]3[C:44]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[C:38]4[C:33]3=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:29]=[CH:30][CH:31]=2)O1>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].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH:34]1[C:33]2[N:32]([C:28]3[CH:27]=[C:26]([C:2]4[CH:3]=[CH:4][C:5]5[N:6]([C:15](=[O:17])[CH3:16])[C:7]6[C:12]([C:13]=5[CH:14]=4)=[CH:11][CH:10]=[CH:9][CH:8]=6)[CH:31]=[CH:30][CH:29]=3)[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1

참가 물질

7

반응물 2

HCID 17148799-Acetyl-3-bromocarbazoleHCID 586908999-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

생성물 1

HCID 710601571-(3-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)ethanone수율 94%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A solution of 1-(3-bromo-9H-carbazol-9-yl)ethanone (2.000 g, 6.94 mmol), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (2.56 g, 6.94 mmol), Pd2(dba)3 (0.064 g, 0.069 mmol), SPhos (0.057 g, 0.139 mmol) and potassium phosphate tribasic hydrate (4.80 g, 20.82 mmol) in toluene (100 mL) and water (10 mL) was stirred at 70° C. under nitrogen overnight. After cooling to room temperature, the organic phase was isolated. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM (1:4, v/v) as eluent to yield 1-(3-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)ethanone (2.9 g, 94%) as a white solid.

후처리

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

출처 및 근거

ORD 기록
ord-8ff4e04a4c12455c97af41ea10863806
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748012B2

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