Cesium carbonate → 2-Chloro-5-(2,2-dimethylpropoxy)pyridine

HRID 242242

Reaction equation

HRID 242242 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.I[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 592802202-Chloro-5-(2,2-dimethylpropoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

5.2 g (40.0 mmol) 6-chloropyridin-3-ol, 11.9 g (60.0 mmol) 1-iodo-2,2-dimethylpropane, 19.6 g (60.0 mmol) cesium carbonate and 120 ml diethylene glycol dimethyl ether are divided into five portions of equal size and are reacted in portions at 160° C. for 4 h in a single mode microwave (CEM Explorer). Thereafter, the five reaction mixtures obtained are combined, the solid is filtered off and rinsed with diethylene glycol dimethyl ether and the filtrate and wash solutions are combined. The majority of the solvent is removed and 300 ml water are added to the concentrated solution (approx. 50 ml). The mixture is stirred for 30 min and the solid obtained is filtered off, washed once with water and dried under a high vacuum.

Workup

  1. customare reacted in portions at 160° C. for 4 h in a single mode microwave (CEM Explorer)
  2. customThereafter, the five reaction mixtures
  3. customobtained
  4. filtrationthe solid is filtered off
  5. washrinsed with diethylene glycol dimethyl ether
  6. washthe filtrate and wash solutions
  7. customThe majority of the solvent is removed
  8. addition300 ml water are added to the concentrated solution (approx. 50 ml)
  9. customthe solid obtained
  10. filtrationis filtered off
  11. washwashed once with water
  12. customdried under a high vacuum

Sources & evidence

ORD record
ord-9515b47fdaa94e3b925ae0dc67765780
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Linked notes

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