Potassium Carbonate → 4,6-Diphenyl-2-[5-(1-naphthyl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine

HRID 2273491Notes

Reaction equation

HRID 2273491 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:16]=[C:17]([C:22]2[N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]=[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:23]=2)[CH:18]=[C:19](Br)[CH:20]=1.C([O-])([O-])=O.[K+].[K+].[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[CH:57]=[CH:56][C:55](B(O)O)=[CH:54][CH:53]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[C:28]1([C:26]2[N:25]=[C:24]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:23]=[C:22]([C:17]3[CH:16]=[C:15]([C:55]4[CH:54]=[CH:53][C:52]([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][N:46]=5)=[CH:57][CH:56]=4)[CH:20]=[C:19]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[CH:18]=3)[N:27]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 679841434,6-Diphenyl-2-[5-(1-naphthyl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazineYield 49%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a stream of argon, 0.37 g (2.14 mmol) of 1-naphthaleneboronic acid, 1.00 g (2.14 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 24.7 mg (0.021 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 80 mL of toluene and 10 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 8.56 mL (8.56 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.64 g (3.21 mmol) of 4-(2-pyridyl)phenylboronic acid wad added. Then the mixture was heated to 70° C. and maintained at that temperature for 3 hours while being stirred. Then 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 obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.61 g of the target 4,6-diphenyl-2-[5-(1-naphthyl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 49%).

Workup

  1. temperatureThen the mixture was heated to 70° C.
  2. temperaturemaintained at that temperature for 3 hours
  3. stirringwhile being stirred
  4. temperatureThen the reaction mixture was cooled to room temperature
  5. distillationwas then distilled under a reduced pressure
  6. customto remove all volatile materials
  7. additionMethanol was added to the concentrate
  8. filtrationthe thus-deposited solid was collected by filtration
  9. customThe obtained crude product
  10. customwas purified by silica gel chromatography
  11. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-e15000ff59ae49dd94c17c60486e9f42
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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