Sodium Carbonate → 4-(4-Bromophenyl)pyridine

HRID 1180373Notes

Reaction equation

HRID 1180373 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 6162834-(4-Bromophenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Pyridin-4-ylboronic acid (500 mg, 4.07 mmol), 1-bromo-4-iodobenzene (1.27 g, 4.47 mmol) and 2M Na2CO3 (6.1 ml, 12.2 mmol) were dissolved in 20 ml DMF and the solution was degassed 3 times. PdCl2(dppf) (149 mg, 0.203 mmol) was added and the mixture was stirred overnight at 80° C. The solution was cooled, poured into 100 ml NaHCO3 (sat.) and extracted 3 times with 20 ml ethyl acetate. The combined organic layers were then washed with 4× water, then dried with Na2SO4. 4-(4-bromophenyl)pyridine was obtained and used without further purification.

Workup

  1. customthe solution was degassed 3 times
  2. temperatureThe solution was cooled
  3. extractionextracted 3 times with 20 ml ethyl acetate
  4. washThe combined organic layers were then washed with 4× water
  5. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-93b3318f9d7043a489f2ccf5a0dca060
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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