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

HRID 1773057Notes

Reaction equation

HRID 1773057 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](C4C=CC(C(C)(C)C)=CC=4)[N:25]=3)[CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)O1.Cl[C:52]1[CH:65]=[CH:64][C:63]2[C:54](=[C:55]3[C:60](=[CH:61][CH:62]=2)[CH:59]=[CH:58][CH:57]=[N:56]3)[N:53]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C.C1(C)C=CC=CC=1>[N:53]1[C:54]2[C:63](=[CH:62][CH:61]=[C:60]3[C:55]=2[N:56]=[CH:57][CH:58]=[CH:59]3)[CH:64]=[CH:65][C:52]=1[C:9]1[CH:14]=[C:13]([C:26]2[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([CH3:37])([CH3:38])[CH3:39])=[CH:32][CH:31]=3)[N:29]=[C:24]([C:11]3[CH:10]=[CH:9][C:14]([C:30]([CH3:35])([CH3:31])[CH3:28])=[CH:13][CH:12]=3)[N:25]=2)[CH:12]=[C:11]([C:57]2[CH:58]=[CH:59][C:60]3[C:55](=[C:54]4[C:63](=[CH:62][CH:61]=3)[CH:64]=[CH:65][CH:52]=[N:53]4)[N:56]=2)[CH:10]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 3551932-Chloro-1,10-phenanthrolineHCID 433294Lithium ChlorideHCID 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 904015782-[3,5-Bis(1,10-phenanthrolin-2-yl)phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 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, 129 mg of 2-chloro-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 2.0 M 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 179 mg of target 2-[3,5-bis(1,10-phenanthrolin-2-yl)phenyl]-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine as a yellow solid (yield, 92%).

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-154444ec8dca491e9c933993da0266f4
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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