Water → 7-Bromo-2-ethyl-4-methoxy-3-nitropyrazolo[1,5-a]pyridine

HRID 1864992

Reaction equation

HRID 1864992 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[Br:9][C:10]1[N:15]2[N:16]=[C:17]([CH2:19][CH3:20])[CH:18]=[C:14]2[C:13]([O:21][CH3:22])=[CH:12][CH:11]=1.O>C(#N)C>[Br:9][C:10]1[N:15]2[N:16]=[C:17]([CH2:19][CH3:20])[C:18]([N+:7]([O-:8])=[O:6])=[C:14]2[C:13]([O:21][CH3:22])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11073463Nitronium tetrafluoroborateHCID 219845677-Bromo-2-ethyl-4-methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 219845347-Bromo-2-ethyl-4-methoxy-3-nitropyrazolo[1,5-a]pyridineYield 47.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding nitronium tetrafluoroborate (176 mg) to a solution of 7-bromo-2-ethyl-4-methoxypyrazolo[1,5-a]pyridine (282 mg) in acetonitrile (20 mL) at 0° C., the mixture was stirred for 20 minutes. Upon completion of the reaction, water was added, extraction was performed with ethyl acetate, the extract washed with saturated aqueous sodium hydrogencarbonate and brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (20 g), and the title compound (159 mg) was obtained from the n-hexane:ethyl acetate (3:1) fraction as yellow crystals.

Workup

  1. additionwas added
  2. extractionextraction
  3. washthe extract washed with saturated aqueous sodium hydrogencarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5209caacfde747999a6936f9d9fb3657
Source dataset
uspto-grants-2009_12
Patent number
US07625925B2

Linked notes

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