Cesium carbonate → 4,6-Diphenyl-2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine

HRID 1773060Notes

Reaction equation

HRID 1773060 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:34]2[CH:47]=[CH:46][C:45]3[C:36](=[C:37]4[C:42](=[CH:43][CH:44]=3)[CH:41]=[CH:40][CH:39]=[N:38]4)[N:35]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]1([C:12]2[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:39]4[CH:40]=[CH:41][C:42]5[C:37](=[C:36]6[C:45](=[CH:44][CH:43]=5)[CH:46]=[CH:47][CH:34]=[N:35]6)[N:38]=4)[CH:3]=3)[N:13]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 589433022-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazineHCID 904015072-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline

Product 1

HCID 904015744,6-Diphenyl-2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, 1.20 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 1.30 g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline, 1.11 g of cesium carbonate, 14 mg of palladium acetate and 32 mg of triphenylphosphine were suspended in 140 mL of tetrahydrofuran. The suspension was heated under reflux for 19 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. Methanol was added to the residue, and the deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel column chromatography using a methanol/chloroform (1:100 to 1:77) mixed solvent as a developing solvent to give 1.37 g of target 4,6-diphenyl-2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine as a white solid (yield, 91%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 19 hours
  3. waitThen the reaction mixture was left
  4. distillationdistilled under a reduced pressure
  5. customto remove low-boiling point ingredients
  6. additionMethanol was added to the residue
  7. filtrationthe deposited solid was collected by filtration
  8. customThe thus-obtained crude product
  9. customwas purified by silica gel column chromatography
  10. additionmixed solvent as a developing solvent
  11. customto give

Sources & evidence

ORD record
ord-eaf9331c2d51414f8a6e7c79b44aa520
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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