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

HRID 626802Notes

Reaction equation

HRID 626802 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N:9]2[CH:18]=[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([F:17])[C:11]3=[N:10]2)=[C:4]([Cl:19])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N:9]2[CH:18]=[C:12]3[CH:13]=[N+:14]([O-:28])[CH:15]=[C:16]([F:17])[C:11]3=[N:10]2)=[C:4]([Cl:19])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 696717852-(4-Bromo-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 677022952-(4-Bromo-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Bromo-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (14.5 g, 40 mmol) was suspended in DCM (160 mL), at 0° C. and meta-chloroperbenzoic acid (12.4 g, 72 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours then allowed to reach room temperature and stirred overnight. Additional meta-chloroperbenzoic acid (5 g, 30 mmol) was added and the reaction mixture was stirred at room temperature 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 and dried to afford the title compound as a beige solid (12.9 g, 86% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.98 (d, J=2.6 Hz, 1H), 8.88 (d, J=1.4 Hz, 1H), 8.33 (dd, J=6.3, 1.5 Hz, 1H), 8.19 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-58ed163ee66f44eda555106ca6325a93
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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