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

HRID 2273501Notes

Reaction equation

HRID 2273501 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][C:35]([CH3:38])=[CH:34][CH:33]=3)[N:29]=[C:28]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)[N:27]=2)[CH:22]=[C:23](Br)[CH:24]=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:35]1([CH3:38])[CH:34]=[CH:33][C:32]([C:30]2[N:29]=[C:28]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)[N:27]=[C:26]([C:21]3[CH:20]=[C:19]([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: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]=1

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 117757049-Phenanthracenylboronic acidHCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 583826282-(3,5-Dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine

Product 1

HCID 866699584,6-Di-p-tolyl-2-[5-(9-phenanthryl)-4'-(2-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, 0.538 g (2.42 mmol) of 9-phenanthreneboronic acid, 1.20 g (2.42 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine and 28.0 mg (0.0242 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 90 mL of toluene and 10 mL of ethanol, and the resultant suspension was heated to 50° 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. The resultant reaction mixture was cooled to room temperature, and then, 0.722 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 to the reaction mixture. The resultant mixture was heated to 60° C., and maintained at that temperature for 15 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and 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 0.680 g of the target 4,6-di-p-tolyl-2-[5-(9-phenanthryl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 42%).

Workup

  1. customThe resultant reaction mixture
  2. temperaturemaintained at that temperature for 15 hours
  3. stirringwhile being stirred
  4. customThe obtained reaction mixture
  5. temperaturewas cooled to room temperature
  6. distillationdistilled under a reduced pressure
  7. customto remove all volatile materials
  8. additionMethanol was added to the concentrate
  9. filtrationthe thus-deposited solid was collected by filtration
  10. customThe obtained crude product
  11. customwas purified by silica gel chromatography
  12. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-da40fc74e002439583cdef7ad077fda0
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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