1,4-Dioxane → HCID 59510699, compound

HRID 2388036Notes

Reaction equation

HRID 2388036 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:19]1[CH:20]=[C:21]([C:37]2[N:42]=[C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:40]=[C:39]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:38]=2)[CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28](C3C=CC=CN=3)=[CH:27][CH:26]=2)[CH:24]=1.O1[CH2:60][CH2:59]OCC1>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N:38]1[CH:60]=[CH:59][CH:20]=[CH:21][C:37]=1[C:1]1[CH:6]=[CH:5][C:4]([C:19]2[CH:20]=[C:21]([C:37]3[N:38]=[C:39]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[N:40]=[C:41]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[N:42]=3)[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:24]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 44138767HCID 44138767, compound

Product 1

HCID 59510699HCID 59510699, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst

Procedure

In a stream of argon, 73 mg of phenylboronic acid, 5.8 mg of tris(dibenzalacetone)dipalldium complex and 12 mg of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were suspended in 15 mL of 1,4-dioxane. 0.6 mL of an aqueous 3N potassium phosphate solution was added to the suspension, and 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 162 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: >99%).

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-9d7480451d644641a60697ff0e79f961
Source dataset
uspto-grants-2012_09
Patent number
US08268997B2

Reaction notes

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