2-Chloropyridine → 3-Chloro-5-(pyridin-2-yloxy)-pyridine

HRID 1959581Notes

Reaction equation

HRID 1959581 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.CC([O-])(C)C.[K+].Cl[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 5823053-Hydroxy-5-chloropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 670774963-Chloro-5-(pyridin-2-yloxy)-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-chloro-pyridin-3-ol (1000 mg, 7.72 mmol), potassium tert-butylate (866 mg, 7.72 mmol) and 2-chloro-pyridine (730 g, 7.72 mmol) in DMF (6 mL) was stirred at 130° C. for 3 h. The solvent was removed in vacuo and the residue was partitioned between DCM (50 mL) and 2 N NaOH solution (50 mL). After extraction of the aqueous layer with DCM (6×50 mL) the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with mixtures of hexane and EA) to give the title compound. MS (m/z): 207.2 [M+H+].

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between DCM (50 mL) and 2 N NaOH solution (50 mL)
  3. extractionAfter extraction of the aqueous layer with DCM (6×50 mL) the combined organic layers
  4. dry with materialwere dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (elution with mixtures of hexane and EA)

Sources & evidence

ORD record
ord-4f8b163bd7784820b517b9b84ba1929d
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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