Sodium Carbonate → 3-(4-Pyridyl)aniline

HRID 1603757Notes

Reaction equation

HRID 1603757 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-640a9d23eb6844f0ad839de2ac1bb8b4
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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