2-(4-Bromophenyl)quinoline → 2-[4,4''-Di(2-quinolyl)-1,1':3',1''-terphenyl-5-yl]-4,6-di-p-tolyl-1,3,5-triazine

HRID 1028918Notes

Reaction equation

HRID 1028918 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].Br[C:24]1[CH:25]=[C:26]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[N:34]=[C:33]([C:44]3[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=3)[N:32]=2)[CH:27]=[C:28](Br)[CH:29]=1>O1CCCC1.CCCCCC.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>[N:9]1[C:8]2[C:21](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:20]=[CH:19][C:18]=1[C:25]1[C:26]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[N:34]=[C:33]([C:44]3[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=3)[N:32]=2)=[CH:27][C:28]([C:15]2[CH:10]=[CH:11][CH:12]=[C:13]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)=[CH:4][CH:3]=3)[CH:14]=2)=[CH:29][CH:24]=1

Participants

7

Reactant 3

HCID 14734442-(4-Bromophenyl)quinolineHCID 583826282-(3,5-Dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazineHCID 178418339Butyllithium

Product 1

HCID 673562442-[4,4''-Di(2-quinolyl)-1,1':3',1''-terphenyl-5-yl]-4,6-di-p-tolyl-1,3,5-triazineYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In a stream of argon, 2.58 g (9.09 mmol) of 2-(4-bromophenyl) quinoline was dissolved in 20 mL of tetrahydrofuran. To the thus-obtained solution, 6.01 mL of a solution in hexane of 9.70 mmol of butyllithium was dropwise added at −78° C. The resultant mixture was stirred at −78° C. for 15 minutes, and then 2.45 g (9.70 mmol) of dichloro(tetramethylethylene-diamine)zinc(II) was added. Temperature of the resultant mixture was elevated to room temperature, and stirred for 1.5 hours. The resultant mixture, and 1.50 g (3.03 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine, and 420 mg (0.364 mmol) of tetrakis(triphenylphosphine)palladium were suspended in 30 mL of tetrahydrofuran, and the obtained suspension was heated under reflux with stirring for 15 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove low boiling ingredients. Methanol was added to the concentrate and the thus-deposited solid was filtered. The thus-obtained crude product was purified by silica gel chromatography using a methanol/chloroform (1:100-2:100) mixed liquid as a developing solvent to give 2.03 g of the target 2-[4,4″-di(2-quinolyl)-1,1′:3′,1″-terphenyl-5-yl]-4,6-di-p-tolyl-1,3,5-triazine as a white solid (yield: 90%).

Workup

  1. customwas elevated to room temperature
  2. temperaturethe obtained suspension was heated
  3. temperatureunder reflux
  4. stirringwith stirring for 15 hours
  5. distillationwas then distilled under a reduced pressure
  6. customto remove low boiling ingredients
  7. additionMethanol was added to the
  8. concentrationconcentrate
  9. filtrationthe thus-deposited solid was filtered
  10. customThe thus-obtained crude product
  11. customwas purified by silica gel chromatography
  12. additionmixed liquid as a developing solvent

Sources & evidence

ORD record
ord-8be869e0c42940d3830baafcdbcb0d6e
Source dataset
uspto-grants-2014_05
Patent number
US08735577B2

Reaction notes

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