Potassium Carbonate → 4,6-Bis(biphenyl-3-yl)-2-[5-(9-phenathryl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine

HRID 2273493Notes

Reaction equation

HRID 2273493 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:18]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[N:29]=[C:28]([C:30]3[CH:31]=[C:32]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:33]=[CH:34][CH:35]=3)[N:27]=[C:26]([C:42]3[CH:47]=[C:46](Br)[CH:45]=[C:44](Br)[CH:43]=3)[N:25]=2)[CH:19]=1.C([O-])([O-])=O.[K+].[K+].[N:62]1[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=1[C:68]1[CH:73]=[CH:72][C:71](B(O)O)=[CH:70][CH:69]=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:18]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[N:29]=[C:28]([C:30]3[CH:31]=[C:32]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:33]=[CH:34][CH:35]=3)[N:27]=[C:26]([C:42]3[CH:47]=[C:46]([C:71]4[CH:70]=[CH:69][C:68]([C:63]5[CH:64]=[CH:65][CH:66]=[CH:67][N:62]=5)=[CH:73][CH:72]=4)[CH:45]=[C:44]([C:13]4[C:14]5[C:5]([C:6]6[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=6[CH:12]=4)=[CH:4][CH:3]=[CH:2][CH:1]=5)[CH:43]=3)[N:25]=2)[CH:19]=1

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 117757049-Phenanthracenylboronic acidHCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 469003312-(3,5-Dibromophenyl)-4,6-bis(biphenyl-3-yl)-1,3,5-triazine

Product 1

HCID 885424114,6-Bis(biphenyl-3-yl)-2-[5-(9-phenathryl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazineYield 58%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a stream of argon, 0.54 g (2.42 mmol) of 9-phenanthreneboronic acid, 1.50 g (2.42 mmol) of 4,6-bis(biphenyl-3-yl)-2-(3,5-dibromophenyl)-1,3,5-triazine and 56.0 mg (0.048 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 150 mL of toluene and 20 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 7.26 mL (7.26 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 0.72 g (3.63 mmol) of 4-(2-pyridyl)phenylboronic acid and 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60° C. and maintained at that temperature for 4 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 1.1 g of the target 4,6-bis(biphenyl-3-yl)-2-[5-(9-phenathryl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 58%).

Workup

  1. temperatureThen the mixture was heated to 60° C.
  2. temperaturemaintained at that temperature for 4 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-161bfb95719b4119a32992d9984ebc0d
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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