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

HRID 2273492Notes

Reaction equation

HRID 2273492 reaction equation
[C:1]1(B(O)O)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.Br[C:21]1[CH:22]=[C:23]([C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:31]=[C:30]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:29]=2)[CH:24]=[C:25](Br)[CH:26]=1.C([O-])([O-])=O.[K+].[K+].[N:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[C:58]1[CH:63]=[CH:62][C:61](B(O)O)=[CH:60][CH:59]=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:34]1([C:32]2[N:31]=[C:30]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:29]=[C:28]([C:23]3[CH:22]=[C:21]([C:61]4[CH:60]=[CH:59][C:58]([C:53]5[CH:54]=[CH:55][CH:56]=[CH:57][N:52]=5)=[CH:63][CH:62]=4)[CH:26]=[C:25]([C:1]4[C:14]5[C:15]6=[C:16]7[C:11](=[CH:12][CH:13]=5)[CH:10]=[CH:9][CH:8]=[C:7]7[CH:6]=[CH:5][C:4]6=[CH:3][CH:2]=4)[CH:24]=3)[N:33]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 5084102Pyren-1-ylboronic acidHCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 866699514,6-Diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazineYield 26%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a stream of argon, 0.53 g (2.14 mmol) of 1-pyreneboronic acid, 1.00 g (2.14 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 24.7 mg (0.0214 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 0.37 g of the target 4,6-diphenyl-2-[5-(1-pyrenyl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 26%).

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-6cc6bb834f5f47a1a91410bbd1844c10
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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