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

HRID 1966927Notes

Reaction equation

HRID 1966927 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-1f860b6a2256411b9fb06dc1a284974e
Source dataset
uspto-grants-2013_04
Patent number
US08420676B2

Reaction notes

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