Nitronium tetrafluoroborate → HCID 21084116, compound

HRID 2253373Notes

Reaction equation

HRID 2253373 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:13]=[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([Br:12])[N:6]2[N:5]=1.F[B-](F)(F)F.[O:19]=[N+:20]=[O:21]>C(#N)C>[CH3:1][O:2][CH2:3][C:4]1[C:13]([N+:20]([O-:21])=[O:19])=[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([Br:12])[N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 21084117HCID 21084117, compound

Product 1

HCID 21084116HCID 21084116, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (7-bromopyrazolo[1,5-a]pyridin-2-yl)methyl methyl ether (1.0 g) dissolved in acetonitrile (20 mL) was added nitronium tetrafluoroborate (606 mg) while stirring on ice. The obtained reaction mixture was added to ice water, extracted with ethyl acetate and then washed with water and brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (546 mg) was obtained as light yellow crystals from the n-hexane:ethyl acetate (5:1) fraction.

Workup

  1. customThe obtained reaction mixture
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. extractionThe obtained organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca04a478fb994fdca3eec2d74b72dbe5
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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