Trifluoroacetic acid → 3-(3-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine

HRID 34086Notes

Reaction equation

HRID 34086 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:11]=3[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 689269803-(3-Fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 597969203-(3-fluorophenyl)-1H-pyrazolo[4,3-c]pyridineYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12 mg of 3-(3-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine in 2 mL of dichloromethane was added 1 mL of trifluoroacetic acid at room temperature and stirred at this temperature for 10 minutes. The reaction solution was poured into aqueous sodium hydrogen carbonate, extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:3), to afford 4 mg of the title compound as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:3)

Sources & evidence

ORD record
ord-c89b8a8617b04d15a6a79267446035ca
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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