Pyridine → 5-Bromo-2-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine

HRID 1752949Notes

Reaction equation

HRID 1752949 reaction equation
N1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=2)=[N:4][N:3]=N1.N1C=CC=CC=1.[C:19](OCC)(=[O:21])[CH3:20]>C(OC(=O)C)(=O)C>[CH3:20][C:19]1[O:21][C:5]([C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 234386835-Bromo-2-(2H-tetrazol-5-yl)pyridine

Product 1

HCID 234386435-Bromo-2-(5-methyl-1,3,4-oxadiazol-2-yl)pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

In 130 ml of acetic anhydride was dissolved 8.6 g of 2-(tetrazol-5-yl)-5-bromopyridine prepared in the Preparation example 6. And then the solution was added with 15 ml of pyridine and stirred for 3 hours for reaction. The reaction mixture was added with ethyl acetate and extracted to separate organic layer. And then the organic layer was washed with water and brine. The organic layer was dehydrated, filtrated and concentrated in vacuo to give 7.3 g of the title compound. Yield 80%.

Workup

  1. customprepared in the Preparation example 6
  2. extractionextracted
  3. customto separate organic layer
  4. washAnd then the organic layer was washed with water and brine
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-922b978cd7784d899d3e8bca634c9442
Source dataset
uspto-grants-2015_10
Patent number
US09163043B2

Reaction notes

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