Sodium Carbonate → 2-[3,5-Bis(1,10-phenanthrolin-4-yl)phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine

HRID 1773058Notes

Reaction equation

HRID 1773058 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:24]3[N:29]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=4)[N:27]=[C:26]([C:40]4[CH:45]=[CH:44][C:43]([C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:42][CH:41]=4)[N:25]=3)[CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)O1.Br[C:52]1[C:65]2[C:56](=[C:57]3[C:62](=[CH:63][CH:64]=2)[CH:61]=[CH:60][CH:59]=[N:58]3)[N:55]=[CH:54][CH:53]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>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>[N:55]1[C:56]2[C:65](=[CH:64][CH:63]=[C:62]3[C:57]=2[N:58]=[CH:59][CH:60]=[CH:61]3)[C:52]([C:13]2[CH:12]=[C:11]([C:24]3[N:25]=[C:26]([C:40]4[CH:41]=[CH:42][C:43]([C:46]([CH3:47])([CH3:48])[CH3:49])=[CH:44][CH:45]=4)[N:27]=[C:28]([C:30]4[CH:31]=[CH:32][C:33]([C:36]([CH3:39])([CH3:37])[CH3:38])=[CH:34][CH:35]=4)[N:29]=3)[CH:10]=[C:9]([C:61]3[C:62]4[C:57](=[C:56]5[C:65](=[CH:64][CH:63]=4)[CH:52]=[CH:53][CH:54]=[N:55]5)[N:58]=[CH:59][CH:60]=3)[CH:14]=2)=[CH:53][CH:54]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 117370304-Bromo-1,10-phenanthrolineHCID 679856612-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine

Product 1

HCID 904016202-[3,5-Bis(1,10-phenanthrolin-4-yl)phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a stream of argon, 168 mg of 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine, 155 mg of 4-bromo-1,10-phenanthroline, 32 mg of lithium chloride and 23 mg of tetrakis(triphenylphosphine)palladium were suspended in a toluene (6.0 mL)/ethanol (1.5 mL) mixed solvent. 1.0 mL of a 2.0M aqueous sodium carbonate solution was added in the obtained suspension, and the mixture was stirred at 100° C. for 88 hours. Then the reaction mixture was left to be cooled to room temperature, and distilled under a reduced pressure to remove low-boiling point ingredients. Water was added to the residue to give a crude product. The crude product was collected by filtration, and evaporated to dryness under a reduced pressure. The dried crude product was recrystallized from a dichloromethane/hexane mixed solvent to give 169 mg of target 2-[3,5-bis(1,10-phenanthrolin-4-yl)phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine as a white solid (yield, 87%).

Workup

  1. additionmixed solvent
  2. waitThen the reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. distillationdistilled under a reduced pressure
  5. customto remove low-boiling point ingredients
  6. additionWater was added to the residue
  7. customto give a crude product
  8. filtrationThe crude product was collected by filtration
  9. customevaporated to dryness under a reduced pressure
  10. customThe dried crude product
  11. customwas recrystallized from a dichloromethane/hexane mixed solvent
  12. customto give

Sources & evidence

ORD record
ord-caabf1ae35554d2cb33ea1ee1fffb80d
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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