Toluene → 2-[5-(9-Anthryl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine

HRID 2273490Notes

Reaction equation

HRID 2273490 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:10]=2)[CH:5]=[C:6](Br)[CH:7]=1.[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+].[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=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>[CH:31]1[C:32]2[C:27](=[CH:33][C:3]3[C:4]([C:9]=2[C:2]2[CH:3]=[C:4]([C:9]4[N:10]=[C:11]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:12]=[C:13]([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:14]=4)[CH:5]=[C:6]([C:49]4[CH:50]=[CH:51][C:46]([C:41]5[CH:42]=[CH:43][CH:44]=[CH:45][N:40]=5)=[CH:47][CH:48]=4)[CH:7]=2)=[CH:5][CH:6]=[CH:7][CH:2]=3)[CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium Carbonate2×HCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 866699502-[5-(9-Anthryl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

In a stream of argon, 0.98 g (3.21 mmol) of 9-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)anthracene, 1.50 g (3.21 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 37.1 mg (0.032 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 100 mL of toluene and 20 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 3 hours. Then the mixture was cooled to room temperature, and 0.96 g (4.82 mmol) of 4-(2-pyridyl)phenylboronic acid and 6.42 mL (6.42 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60° C. and maintained at that temperature for 17 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 0.68 g of the target 2-[5-(9-anthryl)-4′-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 330).

Workup

  1. temperatureThen the mixture was heated to 60° C.
  2. temperaturemaintained at that temperature for 17 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-a65c4c4ce36640a3b9feff0c8f515dc5
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

Loading…