1,1'-Carbonyldiimidazole → 8-bromo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 1777774Notes

Reaction equation

HRID 1777774 reaction equation
[Br:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>C1COCC1.O.CCOC(C)=O>[Br:1][C:2]1[C:3]2[N:4]([C:10](=[O:11])[NH:9][N:8]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 509994063-Bromo-2-hydrazinopyridine

Product 1

HCID 671876628-bromo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 35.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-4 (5.0 g, 26.6 mmol) in THF (50 mL) was added carbonyldiimidazole (5.61 g, 34.6 mmol), and the heterogeneous mixture was stirred for 2 h. The reaction was diluted with water (150 mL) and EtOAc (150 mL), causing a precipitate to form. The mixture was filtered through a sintered glass filter, yielding 2.0 g (35%) of 1-5 as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ12.73 (s, 1H), 7.88 (dd, J=7.2, 0.9 Hz, 1H), 7.58 (dd, J=7.2, 0.9 Hz, 1H), 6.51 (app t, J=7.2 Hz, 1H).

Workup

  1. customto form
  2. filtrationThe mixture was filtered through a sintered glass
  3. filtrationfilter

Sources & evidence

ORD record
ord-d31fbade04944a5ca91765771b39c816
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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