Cesium carbonate → 2-[4'-(1,10-Phenanthrolin-2-yl) biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine

HRID 1773062Notes

Reaction equation

HRID 1773062 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:39]=[CH:38][C:37]([C:40]3[CH:53]=[CH:52][C:51]4[C:42](=[C:43]5[C:48](=[CH:49][CH:50]=4)[CH:47]=[CH:46][CH:45]=[N:44]5)[N:41]=3)=[CH:36][CH: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>[N:41]1[C:42]2[C:51](=[CH:50][CH:49]=[C:48]3[C:43]=2[N:44]=[CH:45][CH:46]=[CH:47]3)[CH:52]=[CH:53][C:40]=1[C:37]1[CH:38]=[CH:39][C:34]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:12]3[N:13]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=4)[N:9]=[C:10]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:11]=3)[CH:19]=2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 583404452-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolineHCID 589433022-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 904016452-[4'-(1,10-Phenanthrolin-2-yl) biphenyl-3-yl]-4,6-diphenyl-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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-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. The thus-deposited solid was collected by filtration, and 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 2-[4′-(1,10-phenanthrolin-2-yl) biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield, 79%).

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 thus-deposited solid was collected by filtration
  8. custompurified by silica gel column chromatography
  9. additionmixed solvent as a developing solvent
  10. customto give

Sources & evidence

ORD record
ord-9ab4d87f8c144fe9853452a1cf7693f0
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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