Tris(1,1-dimethylethyl)phosphine → 11-(4-Carbazolylphenyl)indolo[2,3-a]carbazole

HRID 408067

反応式

HRID 408067 の反応式
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:14]1[C:19]2[N:20]=[C:21]3[C:33]4[C:25]([C:26]5[C:31]([N:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:17]=[CH:16][CH:15]=1.[C:34]1([C:47]2[CH:48]=[C:49](Br)[CH:50]=[CH:51][CH:52]=2)[C:46]2[NH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:34]1([C:47]2[CH:48]=[CH:49][C:50]([N:20]3[C:21]4[C:22](=[CH:23][CH:24]=[C:25]5[C:26]6[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=6[NH:32][C:33]5=4)[C:18]4[C:19]3=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:51][CH:52]=2)[C:46]2[NH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1

参加物

8

反応物 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 21882147Indolo[2,3-a]carbazoleHCID 23676156Sodium t-butoxideHCID 669373163-Carbazolylbromobenzene

生成物 1

HCID 6693759811-(4-Carbazolylphenyl)indolo[2,3-a]carbazole収率 47%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 7237O-Xylene溶媒

反応条件

温度
60 °C

実験手順

In a 100-ml three-necked flask that had been deaerated and filled with nitrogen was placed a solution of 0.21 g (0.94 millimole) of palladium(II) acetate, 0.76 g (3.8 millimoles) of tri-tert-butylphosphine was added, and the mixture was heated at 60° C. with stirring for 30 minutes. The resulting solution was transferred under nitrogen flow to a solution heated at 60° C. of 4.6 g (18.0 millimoles) of indolo[2,3-a]carbazole, 5.8 g (18.0 millimoles) of 3-carbazolylbromobenzene, and 7.7 g (80.0 millimoles) of sodium tert-butoxide in 180 ml of xylene. The solution was then heated to 130° C., and heated with stirring at this temperature for 5 hours. The solution was cooled to room temperature and 200 ml of water was added. The mixture was subjected to oil-water separation, and the organic layer was concentrated under reduced pressure to give a crude product. The crude product was purified by crystallization from dichloromethane and ethanol, the solvent was stripped off under reduced pressure, and 4.2 g (8.4 millimoles, 47% yield) of 11-(4-carbazolylphenyl)indolo[2,3-a]carbazole was obtained.

後処理

  1. customIn a 100-ml three-necked flask that had been deaerated
  2. additionfilled with nitrogen
  3. additionwas added
  4. temperatureThe solution was then heated to 130° C.
  5. temperatureheated
  6. stirringwith stirring at this temperature for 5 hours
  7. temperatureThe solution was cooled to room temperature
  8. customThe mixture was subjected to oil-water separation
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. customto give a crude product
  11. customThe crude product was purified by crystallization from dichloromethane and ethanol

出典と根拠

ORDレコード
ord-a9948952bf76433eafe4ea80146ae1c3
出典データセット
uspto-grants-2014_06
特許番号
US08758904B2

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