1,1'-Carbonyldiimidazole → 6-bromo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

HRID 2368017Notes

Reaction equation

HRID 2368017 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10](=[O:11])[NH:9][N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 120407986-bromo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 40 g 5-bromo-2-hydrazinylpyridine (212 mmol) and 38 g 1,1′-Carbonyldiimidazole (234 mmol) in 500 mL acetonitrile was refluxed for 2 h. The reaction was then cooled to room temperature overnight. The precipitate was collect by filtration. 6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one as a light brown solid was collected. m/z (ESI)=213.9 [M+H]+. 1H NMR (δ, d6-DMSO, 400 MHz) 12.59 (s, 1H), 8.04 (dd, 1H), 7.21 (m, 2H).

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationThe precipitate was collect by filtration
  3. custom6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one as a light brown solid was collected

Sources & evidence

ORD record
ord-4564263c04f6480598dca5d81065fc7b
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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