Cesium carbonate → HCID 59510699, compound

HRID 2388037Notes

Reaction equation

HRID 2388037 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:17]1[CH:18]=[C:19]([C:35]2[N:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[C:37]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:36]=2)[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26](C3C=CC=CN=3)=[CH:25][CH:24]=2)[CH:22]=1.O1[CH2:58][CH2:57]OCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N:36]1[CH:58]=[CH:57][CH:18]=[CH:19][C:35]=1[C:1]1[CH:6]=[CH:5][C:4]([C:17]2[CH:18]=[C:19]([C:35]3[N:36]=[C:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:38]=[C:39]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[N:40]=3)[CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:22]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 44138767HCID 44138767, compound

Product 1

HCID 59510699HCID 59510699, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst

Procedure

In a stream of argon, 73 mg of phenylboronic acid, 2.9 mg of palladium acetate, 195 mg of cesium carbonate and 12 mg of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were suspended in 15 mL of 1,4-dioxane. The obtained mixture was stirred at room temperature for 10 minutes. To this mixture, 149 mg of 2-[5-chloro-4′-(2-pyridyl)-1,1′-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine, synthesized in Example 1, was added, and the resultant mixture was refluxed under heating at 110° C. for 48 hours. Then the reaction mixture was left to stand at room temperature, and was concentrated under a reduced pressure to give a solid. The solid was purified by silica gel chromatography using a hexane/chloroform mixed liquid (50:50-0:100) as a developing solvent, and then recrystallized from dichloromethane/methanol to give 153 mg of 2-{4-(2-pyridyl)-[1,1′:3′,1″]-terphenyl-5′-yl}-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 95%).

Workup

  1. additionwas added
  2. temperatureunder heating at 110° C. for 48 hours
  3. waitThen the reaction mixture was left
  4. customto stand at room temperature
  5. concentrationwas concentrated under a reduced pressure
  6. customto give a solid
  7. customThe solid was purified by silica gel chromatography
  8. customrecrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-218d62a1fc3d4bbf8274371daaea77b4
Source dataset
uspto-grants-2012_09
Patent number
US08268997B2

Reaction notes

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