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

HRID 2273495Notes

Reaction equation

HRID 2273495 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.Br[C:19]1[CH:20]=[C:21]([C:26]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:27]=2)[CH:22]=[C:23](Br)[CH:24]=1.C([O-])([O-])=O.[K+].[K+].[N:50]1[CH:55]=[CH:54][CH:53]=[C:52]([C:56]2[CH:57]=[C:58](B(O)O)[CH:59]=[CH:60][CH:61]=2)[CH:51]=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:32]1([C:30]2[N:29]=[C:28]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:27]=[C:26]([C:21]3[CH:20]=[C:19]([C:58]4[CH:59]=[CH:60][CH:61]=[C:56]([C:52]5[CH:51]=[N:50][CH:55]=[CH:54][CH:53]=5)[CH:57]=4)[CH:24]=[C:23]([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:22]=3)[N:31]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 117757049-Phenanthracenylboronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazineHCID 58526507(3-(Pyridin-3-yl)phenyl)boronic acid

Product 1

HCID 866699534,6-Diphenyl-2-[5-(9-phenanthryl)-3'-(3-pyridyl)biphenyl-3-yl]-1,3,5-triazineYield 42%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a stream of argon, 0.71 g (3.21 mmol) of 9-phenanthreneboronic acid, 1.50 g (3.21 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 37.0 mg (0.0321 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 120 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 9.63 mL (9.63 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 8 hours. Then the mixture was cooled to room temperature, and 0.59 g (4.82 mmol) of 3-(3-pyridyl)phenylboronic acid and 9.63 mL (9.63 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60° C. and maintained at that temperature for 18 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 0.86 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-3′-(3-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 42%).

Workup

  1. temperatureThen the mixture was heated to 60° C.
  2. temperaturemaintained at that temperature for 18 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-a278b082335648f698dec51cb4564cdc
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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