4-Aminobiphenyl → HCID 58672293, compound

HRID 868790Notes

Reaction equation

HRID 868790 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:22]=2)=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:3][C:2]([NH:1][C:30]2[CH:29]=[CH:28][C:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([C:18]4[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=4)[CH:22]=3)=[CH:32][CH:31]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 71024-AminobiphenylHCID 144525341~4~-Bromo-1~1~,2~1~:2~3~,3~1~-terphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 58672293HCID 58672293, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

In a drybox, 4-aminobiphenyl (0.542 g) and 4-bromo-1,1′:3′,1″-terphenyl (0.89 g) were combined in a round-bottom flask and dissolved in 10 ml of dry toluene. Tris(tert-butyl)phosphine (0.022 g, 0.11 mmol) and tris(dibenzylideneacetone) dipalladium(0) (0.05 g, 0.055 mmol) were dissolved in 10 ml of dry toluene and stirred for 5 minutes. The catalyst solution was added to the reaction mixture, stirred for 2 minutes and was followed by sodium tert-butoxide (0.32 g, 3.3 mmol). Flask was capped and left to stir in the drybox overnight at room temperature. Next day, reaction mixture was taken out of the box and filtered through a one-inch plug of silica gel topped with celite, washing with 500 ml of dichloromethane. Removal of volatiles under reduced pressure gave a yellow solid. Crude product was purified by trituration with diethyl ether to give 0.85 g (73%) of a white solid. Structure was confirmed by 1H NMR spectroscopy.

Workup

  1. additionThe catalyst solution was added to the reaction mixture
  2. stirringstirred for 2 minutes
  3. customFlask was capped
  4. waitleft
  5. stirringto stir in the drybox overnight at room temperature
  6. customNext day, reaction mixture
  7. filtrationfiltered through a one-inch plug of silica gel
  8. washwashing with 500 ml of dichloromethane
  9. customRemoval of volatiles under reduced pressure
  10. customgave a yellow solid
  11. customCrude product was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-9e56fd8d9f8c464c8a8900f608571574
Source dataset
uspto-grants-2015_03
Patent number
US08968883B2

Reaction notes

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