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

HRID 634557

Reaction equation

HRID 634557 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6adf938bce554fbb8bc9c7ee97c9dd54
Source dataset
uspto-grants-2016_04
Patent number
US09324954B2

Linked notes

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