Potassium Carbonate → 1-(5-Chloro-2-nitrophenyl)-1H-[1,2,3]triazolo[4,5-b]pyridine

HRID 502832Notes

Reaction equation

HRID 502832 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH:12]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[N:13]2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 178420751HCID 178420751, compound

Product 1

HCID 575389621-(5-Chloro-2-nitrophenyl)-1H-[1,2,3]triazolo[4,5-b]pyridineYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-2-fluoro-1-nitrobenzene (25 g, 142 mmol) and 1H-[1,2,3]triazolo[4,5-b]pyridine (18.8 g, 157 mmol) were slurried in DMF (50 mL) in a 200 mL round-bottom flask fitted with a magnetic stir bar. Potassium carbonate (29.5 g, 214 mmol) was added to the mixture and it was then heates while stirring in a 60°C. oil bath under N2. LCMS analysis after two hours indicated complete consumption of the nitrobenzene and two different isomeric forms of the desired product. Water (250 mL) was subsequently added in a steady stream to the rapidly stirring mixture to precipitate the crude product. The resultant precipitate was collected by vacuum filtration and washed twice with 100 mL water. The resultant damp filter was slurried with 50 mL toluene and the solids collected by vacuum filtration. This action was repeated three additional times and then the resultant solid was dried in vacuo to afford 21.6 g (55% yield) 1-(5-chloro-2-nitrophenyl)-1 H-[1,2,3]triazolo[4,5-b]pyridine as an off-white solid.

Workup

  1. customfitted with a magnetic stir bar
  2. customconsumption of the nitrobenzene and two different isomeric forms of the desired product
  3. additionWater (250 mL) was subsequently added in a steady stream to the
  4. stirringrapidly stirring mixture
  5. customto precipitate the crude product
  6. filtrationThe resultant precipitate was collected by vacuum filtration
  7. washwashed twice with 100 mL water
  8. filtrationThe resultant damp filter
  9. filtrationthe solids collected by vacuum filtration
  10. customthe resultant solid was dried in vacuo

Sources & evidence

ORD record
ord-42c12133494e47db87363b00d0f71228
Source dataset
uspto-grants-2010_08
Patent number
US07776877B2

Reaction notes

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