2-chloro-benzoic acid N'-(5-bromo-pyridin-2-yl)hydrazide → 6-Bromo-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 2252318Notes

Reaction equation

HRID 2252318 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[N:6][CH:7]=1>O=P(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:9][N:8]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 692020042-chloro-benzoic acid N'-(5-bromo-pyridin-2-yl)hydrazide

Product 1

HCID 179744786-Bromo-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridineYield 30.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-chloro-benzoic acid N′-(5-bromo-pyridin-2-yl)hydrazide (2.96 g, 9.1 mmol) in POCl3 (15 mL) was heated at 85° C. for 48 hours. The solvent was removed in vacuo, and the residue quenched with saturated Na2CO3 and EtOAc. The layers were separated, and the organic layer concentrated in vacuo to minimal volume. The resulting solid was filtered and purified by flash chromatography to give the title compound (0.85 g, 30%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue quenched with saturated Na2CO3 and EtOAc
  3. customThe layers were separated
  4. concentrationthe organic layer concentrated in vacuo to minimal volume
  5. filtrationThe resulting solid was filtered
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e69de3ba1c004d21b1ba54520bbbb072
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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