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

HRID 1773056Notes

Reaction equation

HRID 1773056 reaction equation
Br[C:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[N:8]3)[N:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:25]=[C:26]([C:39]3[N:44]=[C:43]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:42]=[C:41](C4C=CC=CC=4)[N:40]=3)[CH:27]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)O1.[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:5]1[C:6]2[C:15](=[CH:14][CH:13]=[C:12]3[C:7]=2[N:8]=[CH:9][CH:10]=[CH:11]3)[C:2]([C:6]2[CH:7]=[C:12]([C:41]3[N:42]=[C:43]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:44]=[C:39]([C:26]4[CH:25]=[CH:24][CH:29]=[CH:28][CH:27]=4)[N:40]=3)[CH:13]=[C:14]([C:11]3[C:12]4[C:7](=[C:6]5[C:15](=[CH:14][CH:13]=4)[CH:2]=[CH:3][CH:4]=[N:5]5)[N:8]=[CH:9][CH:10]=3)[CH:15]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 117370304-Bromo-1,10-phenanthrolineHCID 583826222-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 904015612-[3,5-Bis(1,10-phenanthrolin-4-yl)phenyl]-4,6-diphenyl-1,3,5-triazine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a stream of argon, 1.42 g of 4-bromo-1,10-phenanthroline, 1.29 g 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine, 515 mg of lithium chloride and 266 mg of tetrakis(triphenylphosphine)palladium were suspended in a toluene (52 mL)/ethanol (13 mL) mixed solvent. 9.2 mL of a 2.0 M aqueous sodium carbonate solution was added in the suspension, and the mixture was stirred at 100° C. for 94 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. The obtained crude product was purified by alumina column chromatography using a hexane/chloroform (1:1 to 0:1) mixed solvent as a developing solvent to give 955 mg of target 2-[3,5-bis(1,10-phenanthrolin-4-yl)phenyl]-4,6-diphenyl-1,3,5-triazine as a white powder (yield, 62%).

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. customThe obtained crude product
  7. customwas purified by alumina column chromatography
  8. additionmixed solvent as a developing solvent
  9. customto give

Sources & evidence

ORD record
ord-46cb9da719e041789cbf9584858ad20d
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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