4-Aminobenzonitrile → 4-Cyanophenyl,3-(3,6-diphenyl-9-carbazolyl)phenylaniline

HRID 921602

반응식

HRID 921602 반응식
C1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:27]=[C:28](Br)[CH:29]=[CH:30][CH:31]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=4)C=CC=CC=1.[NH2:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=1.C(P([C:51]([CH3:54])([CH3:53])C)C(C)(C)C)(C)(C)C.[C:55](O[Na])([CH3:58])([CH3:57])C>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:38]([C:37]1[CH:40]=[CH:41][C:34]([N:33]([C:8]2[CH:7]=[CH:19][CH:18]=[C:10]([N:11]3[C:12]4[CH:13]=[CH:14][C:15]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:16][C:17]=4[C:27]4[C:26]3=[CH:31][CH:30]=[C:29]([C:53]3[CH:51]=[CH:54][CH:18]=[CH:10][CH:9]=3)[CH:28]=4)[CH:9]=2)[C:57]2[CH:55]=[CH:58][CH:8]=[CH:7][CH:19]=2)=[CH:35][CH:36]=1)#[N:39]

참가 물질

7

반응물 4

HCID 133964-AminobenzonitrileHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 581422319-(3-bromophenyl)-3,6-diphenyl-9H-CarbazoleHCID 178418730sodium 2-methylpropan-2-olate

생성물 1

HCID 866960804-Cyanophenyl,3-(3,6-diphenyl-9-carbazolyl)phenylaniline수율 80%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

9.0 g of carbazole from step (2b) above and 2.23 g 4-aminobenzonitrile were mixed in 60 mL toluene in nitrogen filled glove box. 0.4 g Pd2DBA3 and 0.18 g tri-t-butylphosphine were added followed quickly by 1.81 g t-BuONa. The mixture was heated briefly to reflux then held at 80° C. overnight in the glove box with vigorous stirring. After cooling the reaction was chromatographed on silica using a gradient of DCM:hexanes (1:4 to 4:1) to elute the product which upon concentration and addition of hexanes precipitated the desired product in ˜80% yield (˜6.5 g) with structure confirmed by 1-H nmr spectroscopy.

후처리

  1. temperatureThe mixture was heated briefly
  2. temperatureto reflux
  3. temperatureAfter cooling the reaction
  4. customwas chromatographed on silica using a gradient of DCM:hexanes (1:4 to 4:1)
  5. washto elute the product which
  6. concentrationupon concentration and addition of hexanes
  7. customprecipitated the desired product in ˜80% yield (˜6.5 g) with structure

출처 및 근거

ORD 기록
ord-d6b58b983ff44ccb81e17d6aeb73a5a6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09276217B2

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