1,1'-Carbonyldiimidazole → 8-Bromo-7-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101300

Reaction equation

HRID 2101300 reaction equation
[Br:1][C:2]1[C:3]([NH:15][NH2:16])=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>C1COCC1>[Br:1][C:2]1[C:3]2[N:4]([C:17](=[O:18])[NH:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 577994543-Bromo-4-(4-chlorophenyl)-2-hydrazinylpyridine

Product 1

HCID 577994388-Bromo-7-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Crude 3-bromo-4-(4-chlorophenyl)-2-hydrazinylpyridine (7 g, 23 mmol) was dissolved in dry THF (100 mL), and the resulting solution was cooled to 0° C. To this was added 1,1′carbonyldiimidazole (18 g, 111 mmol). The reaction mixture was stirred at room temperature for 10 h. The solvent was evaporated under vacuum, and water (10 mL) was added, which caused solid desired product to precipitate. This was filtered, washed with water (2×25 mL), and dried to obtain the title compound as a yellow solid (6.3 g), which was used without further purification.

Workup

  1. customThe solvent was evaporated under vacuum, and water (10 mL)
  2. additionwas added
  3. customto precipitate
  4. filtrationThis was filtered
  5. washwashed with water (2×25 mL)
  6. customdried

Sources & evidence

ORD record
ord-f2374dc14b034ee3ace9ba8e8e5d09e1
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Linked notes

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