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

HRID 2068691Notes

Reaction equation

HRID 2068691 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[N:10][OH:11])[NH2:9])=[N:6][CH:7]=1.[C:12](OC(=O)C)(=O)[CH3:13]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:12]([CH3:13])[O:11][N:10]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 136397847HCID 136397847, compound

Product 1

HCID 234386105-Bromo-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N′-hydroxypicolinimidamide II (0.75 g, 3.50 mmol) in acetic acid (50.0 mL) was added acetic anhydride (0.75 mL, 7.0 mmol) and the resulting reaction mixture was heated to 100° C. for 2 h. After the completion of reaction (TLC monitoring), acetic acid was distilled off, added water (25.0 mL) and extracted with EtOAc (2×50 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated to obtain the desired product (0.27 g, 45%). MS: 240.01 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. distillationwas distilled off
  3. additionadded water (25.0 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe combined organics was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0faa30e588764b6fad944d8e1a0bb74f
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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