m-Chloroperbenzoic acid → 2-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide

HRID 626794Notes

Reaction equation

HRID 626794 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N:14][CH:15]=[C:16]([F:17])[C:11]2=[N:10]1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N+:14]([O-:27])[CH:15]=[C:16]([F:17])[C:11]2=[N:10]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 696713422-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 677014502-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxideYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (9.95 g, 37.5 mmol) was suspended in DCM (150 mL) at 0° C. and meta-chloroperbenzoic acid (12.9 g, 75 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours then allowed to reach room temperature and stirred for another 3 hours. The resultant mixture was quenched with saturated aqueous sodium thiosulfate solution and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether and the solid obtained was filtered off and dried to afford the title compound as a white solid (7.22 g, 68% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.04 (d, J=2.6 Hz, 1H), 8.88 (d, J=1.4 Hz, 1H), 8.35 (dd, J=6.4, 1.5 Hz, 1H), 7.82-7.73 (m, 1H), 7.72-7.62 (m, 2H).

Workup

  1. customto reach room temperature
  2. stirringstirred for another 3 hours
  3. customThe resultant mixture was quenched with saturated aqueous sodium thiosulfate solution
  4. customthe layers were separated
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with diethyl ether
  10. customthe solid obtained
  11. filtrationwas filtered off
  12. customdried

Sources & evidence

ORD record
ord-5be0a2739af841b69d530ffda6f7bd0a
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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