Sodium Carbonate → 3-(4-Pyridyl)aniline

HRID 989169Notes

Reaction equation

HRID 989169 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(=O)([O-])[O-].[Na+].[Na+].[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>COCCOC.O>[N:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=2)[NH2:5])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 4595233-(4-Pyridyl)anilineYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Bromoaniline (0.24 ml, 2.2 mmol) and sodium carbonate (0.70 g, 6.6 mmol) were suspended in a mixture of 1,2-dimethoxyethane (16 ml) and water (4 ml). The reaction mixture was then treated with 4-pyridyl boronic acid (0.27 g, 2.2 mmol), and flushed with Argon. Tetrakis (triphenylphosphine)palladium (0) (0.35 g) was then added and the mixture was heated to reflux under Argon for 24 hours. The reaction mixture was allowed to cool after which it was partitioned between dichloromethane and water. The aqueous layer was again extracted with dichloromethane. The combined extracts were then dried (Na2SO4) and concentrated in vacuo to afford a pale yellow solid (0.35 g). This was chromatographed on silica gel eluting with ethyl acetate to afford the title compound as a white solid (0.15 g, 41%).

Workup

  1. customflushed with Argon
  2. additionTetrakis (triphenylphosphine)palladium (0) (0.35 g) was then added
  3. temperaturethe mixture was heated
  4. temperatureto reflux under Argon for 24 hours
  5. temperatureto cool after which it
  6. customwas partitioned between dichloromethane and water
  7. extractionThe aqueous layer was again extracted with dichloromethane
  8. dry with materialThe combined extracts were then dried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75ff39c51faa4faaa0d104b667996768
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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