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

HRID 634557

반응식

HRID 634557 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 7809P-Xylene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6adf938bce554fbb8bc9c7ee97c9dd54
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09324954B2

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