Pivaloyl chloride → 5-(5-Tert-butyl-1,2,4-oxadiazol-3-yl)-2-chloropyridine

HRID 2199601Notes

Reaction equation

HRID 2199601 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[N:10][OH:11])[NH2:9])=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=O>C1(C)C=CC=CC=1.CC(O)=O>[C:13]([C:18]1[O:11][N:10]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=2)[N:9]=1)([CH3:17])([CH3:14])[CH3:12]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 336784996-Chloro-N-hydroxy-nicotinamidine

Product 1

HCID 866599575-(5-Tert-butyl-1,2,4-oxadiazol-3-yl)-2-chloropyridineYield 21%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1.5 g (8.74 mmol) of 6-chloro-N′-hydroxypyridine-3-carboximidamide and 1.13 mL (9.18 mmol) of trimethylacetyl chloride in 15 mL of toluene is stirred for 1 hour at room temperature and then refluxed for 4 hours. The medium is filtered. The insoluble material formed is dissolved in 15 mL of AcOH and then heated at 60° C. for 5 hours. After cooling to room temperature, the medium is concentrated under reduced pressure and then purified by chromatography on silica gel, eluting with a cyclohexane/EtOAc mixture (9/1). 0.39 g of 5-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-2-chloropyridine is obtained in the form of a white solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationThe medium is filtered
  3. customThe insoluble material formed
  4. temperatureheated at 60° C. for 5 hours
  5. temperatureAfter cooling to room temperature
  6. concentrationthe medium is concentrated under reduced pressure
  7. custompurified by chromatography on silica gel
  8. washeluting with a cyclohexane/EtOAc mixture (9/1)

Sources & evidence

ORD record
ord-4a8e9e75ad194f2fb0e0debe6be07851
Source dataset
uspto-grants-2016_06
Patent number
US09359329B2

Reaction notes

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