Nitronium tetrafluoroborate → HCID 21084113, compound

HRID 2253368Notes

Reaction equation

HRID 2253368 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:17]=[N+:18]=[O:19]>C(#N)C>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[C:10]([N+:18]([O-:19])=[O:17])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 21084115HCID 21084115, compound

Product 1

HCID 21084113HCID 21084113, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 7-bromo-2-methylpyrazolo[1,5-a]pyridine (1.3 g) dissolved in acetonitrile (25 mL) was added nitronium tetrafluoroborate (900 mg) while stirring on ice, and the reaction mixture was stirred for 10 minutes. The obtained reaction mixture was added to ice water, and the precipitated crystals were collected by filtration, washed with water and then dried under reduced pressure to afford crude crystals. These were purified by silica gel column chromatography and the title compound (900 mg) was obtained as yellow crystals from the n-hexane:ethyl acetate (5:1) fraction.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. customThe obtained reaction mixture
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure
  6. customto afford crude crystals
  7. customThese were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff2c3da4decc4a4294800b36899dd5b7
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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