Potassium Carbonate → HCID 23150278, compound

HRID 657668Notes

Reaction equation

HRID 657668 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.O.C(O)C.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>[Cl:12][CH2:11][CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 126856091-Bromo-4-(3-chloropropoxy)benzene

Product 1

HCID 23150278HCID 23150278, compoundYield 53.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 1-bromo-4-(3-chloropropoxy)benzene (1.25 g) and tetrakistriphenylphosphinepalladium (58 mg) in toluene (12 mL) and potassium carbonate (2.07 g) in water (6 mL) is added pyridine-4-boronic acid (380 mg) dissolved in ethanol. The mixture is heated for five hours at a temperature close to 80° C. Solvents are removed under reduced pressure and the residue dissolved in ethyl acetate. The organic phase is washed with a 10% aqueous solution of potassium hydroxide, then with water, dried over magnesium sulfate, filtered and concentrated. The residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5) to give 408 mg of 4-(4-(3-chloropropoxy)phenyl]pyridine as an ochre oil used without further purification.

Workup

  1. temperatureThe mixture is heated for five hours at a temperature
  2. customclose to 80° C
  3. customSolvents are removed under reduced pressure
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe organic phase is washed with a 10% aqueous solution of potassium hydroxide
  6. dry with materialwith water, dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5)

Sources & evidence

ORD record
ord-d32d00276bca4d7eb570e66bbac28362
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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