Potassium Phosphate, Tribasic → HCID 67983927, compound

HRID 2273487Notes

Reaction equation

HRID 2273487 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13](C3C=CC(C4C=NC=CC=4)=CC=3)[CH:12]=[C:11]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)=[CH:29][CH:28]=3)[N:10]=2)[CH:5]=[C:6](Cl)[CH:7]=1.[C:39]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:40](B(O)O)=[CH:41][CH:42]=[CH:43][CH:44]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([C:30]2[CH:31]=[CH:32][C:27]([C:11]3[CH:12]=[C:13]([C:27]4[CH:28]=[CH:29][C:30]([C:33]5[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=5)=[CH:31][CH:32]=4)[N:14]=[C:9]([C:4]4[CH:3]=[C:2]([C:41]5[CH:42]=[CH:43][CH:44]=[C:39]([C:48]6[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=6)[CH:40]=5)[CH:7]=[C:6]([C:43]5[CH:44]=[C:39]([C:48]6[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=6)[CH:40]=[CH:41][CH:42]=5)[CH:5]=4)[N:10]=3)=[CH:28][CH:29]=2)[CH:34]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 4589187Biphenyl-2-boronic acidHCID 67984102HCID 67984102, compound

Product 1

HCID 67983927HCID 67983927, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, 0.45 g (0.85 mmol) of 2-(3,5-dichlorophenyl)-4,6-bis[4-(3-pyridyl)phenyl]pyrimidine, 0.37 g (1.87 mmol) of m-biphenylboronic acid, 0.39 g (1.86 mmol) of potassium phosphate, 8 mg (0.034 mmol) of palladium acetate and 32 mg (0.068 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisipropylbiphenyl were suspended in 20 mL of tetrahydrofuran, and the obtained suspension was heated under reflux for 66 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using chloroform as an eluent to give 0.42 g of the target 4,6-bis[4-(3-pyridyl)phenyl]-2-(1,1′:3′,1″:3″,1″′:3″′,1″″-quinquephenyl-5″-yl)pyrimidine as a white solid (yield: 640).

Workup

  1. temperaturethe obtained suspension was heated
  2. temperatureunder reflux for 66 hours
  3. distillationwas then distilled under a reduced pressure
  4. customto remove all volatile materials
  5. additionMethanol was added to the concentrate
  6. filtrationthe thus-deposited solid was collected by filtration
  7. customThe thus-obtained crude product
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-15c2b71806424eec947b545f9c1be6cb
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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