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

HRID 1913186Notes

Reaction equation

HRID 1913186 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) of 6-chloropyridin-3-ol, 11.9 g (60.0 mmol) of 1-iodo-2,2-dimethylpropane, 19.6 g (60.0 mmol) of cesium carbonate and 120 ml of diethylene glycol dimethyl ether are divided into five portions of equal size and reacted portion-wise in a single-mode microwave oven (CEM Explorer) at 160° C. for 4 h. The five reaction mixtures obtained are then combined, the solid is filtered off and washed with diethylene glycol dimethyl ether and filtrate and wash solutions are combined. Most of the solvent is removed, and 300 ml of water are added to the concentrated (about 50 ml) solution. The mixture is stirred for 30 min, and the solid obtained is filtered off, washed once with water and dried under high vacuum.

Workup

  1. customreacted portion-wise in a single-mode microwave oven (CEM Explorer) at 160° C. for 4 h
  2. customThe five reaction mixtures
  3. customobtained
  4. filtrationthe solid is filtered off
  5. washwashed with diethylene glycol dimethyl ether and filtrate
  6. washwash solutions
  7. customMost of the solvent is removed
  8. addition300 ml of water are added to the
  9. concentrationconcentrated (about 50 ml) solution
  10. customthe solid obtained
  11. filtrationis filtered off
  12. washwashed once with water
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-e099710439f74fff8b4e32d432c86a19
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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