Ethyl Acetate → 7-(2,4-Dichlorophenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

HRID 1864985

Reaction equation

HRID 1864985 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:18][CH3:19])[CH:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1.F[B-](F)(F)F.[O:25]=[N+:26]=[O:27].C(OCC)(=O)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:18][CH3:19])[C:17]([N+:26]([O-:27])=[O:25])=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11073463Nitronium tetrafluoroborateHCID 219846357-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridine

Product 1

HCID 219846667-(2,4-Dichlorophenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridineYield 35.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After dissolving 7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridine (280 mg) in acetonitrile (20 mL), nitronium tetrafluoroborate (255 mg) was added 4 times at 30 minute intervals while stirring on ice. The reaction mixture was added to ice water, extraction was performed with ethyl acetate and the extract washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (115 mg) was obtained from the n-hexane:ethyl acetate (20:1) fraction as yellow crystals.

Workup

  1. additionwas added 4 times at 30 minute intervals
  2. washthe extract washed with water and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2193a05f7a4f4514a0880e7a83c7f38d
Source dataset
uspto-grants-2009_12
Patent number
US07625925B2

Linked notes

Loading…