Tris(1,1-dimethylethyl)phosphine → 9-[3-(4,6-Diphenylpyrimidin-2-yl)phenyl]-9'-phenyl-9H,9'H-[3,3]bicarbazolyl

HRID 634557

反応式

HRID 634557 の反応式
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16]([C:20]4[CH:21]=[CH:22][C:23]5[NH:24][C:25]6[C:30]([C:31]=5[CH:32]=4)=[CH:29][CH:28]=[CH:27][CH:26]=6)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:34]1[CH:35]=[C:36]([C:40]2[N:45]=[C:44]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:43]=[C:42]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:41]=2)[CH:37]=[CH:38][CH:39]=1.CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC1C=CC(C)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:52]1([C:42]2[CH:43]=[C:44]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:45]=[C:40]([C:36]3[CH:35]=[C:34]([N:24]4[C:23]5[CH:22]=[CH:21][C:20]([C:16]6[CH:17]=[CH:18][C:19]7[N:7]([C:1]8[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=8)[C:8]8[C:13]([C:14]=7[CH:15]=6)=[CH:12][CH:11]=[CH:10][CH:9]=8)=[CH:32][C:31]=5[C:30]5[C:25]4=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH:39]=[CH:38][CH:37]=3)[N:41]=2)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

参加物

7

反応物 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 589431812-(3-Bromophenyl)-4,6-diphenylpyrimidineHCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolyl

生成物 1

HCID 585114899-[3-(4,6-Diphenylpyrimidin-2-yl)phenyl]-9'-phenyl-9H,9'H-[3,3]bicarbazolyl

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 7809P-Xylene溶媒

実験手順

22.00 g (53.86 mmol) of 9-phenyl-9H,9′H-[3,3′]bicarbazolyl 26, 22.93 g (59.24 mmol) of 2-(3-bromophenyl)-4,6-diphenylpyrimidine 14 and 15.81 g (164.47 mmol) of NaOtBu are suspended in 820 ml of p-xylene. 244.79 mg (1.09 mmol) of Pd(OAc)2 and 3.3 ml of a 1M tri-tert-butylphosphine solution are added to this suspension. The reaction mixture is heated under reflux for 19 h. After cooling, the organic phase is separated off, washed three times with 100 ml of water and subsequently evaporated to dryness. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum. The yield is 23.10 g (60%).

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 19 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 100 ml of water
  6. customsubsequently evaporated to dryness
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

出典と根拠

ORDレコード
ord-6adf938bce554fbb8bc9c7ee97c9dd54
出典データセット
uspto-grants-2016_04
特許番号
US09324954B2

関連ノート

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