Sodium Thiosulfate → 2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide

HRID 626658Notes

Reaction equation

HRID 626658 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[CH:28]=[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:22]2=[N:21]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[CH:28]=[C:23]2[CH:24]=[N+:25]([O-:9])[CH:26]=[CH:27][C:22]2=[N:21]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 696718102-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 677015532-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dried solution of mCPBA (7.2 mmol) in DCM (20 mL) was added to a cooled (0° C.) solution of 2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (1.28 g, 4.8 mmol) in DCM (30 mL) under nitrogen. The reaction mixture was stirred for 1 hour, warmed to room temperature, and stirred for a further 2 hours. Sodium thiosulfate (sat. aq.) was added and the layers were partitioned. The organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine, dried over anhydrous magnesium sulfate, and concentrated to under reduced pressure. The residue was purified by silica gel flash chromatography (5-10% methanol in DCM) to afford the title compound as a white solid (1.22 g, 91% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.90 (dd, J=1.8, 0.9 Hz, 1H), 8.84 (d, J=1.0 Hz, 1H), 7.95 (dd, J=7.5, 1.8 Hz, 1H), 7.84 (dt, J=7.5, 1.0 Hz, 1H), 7.81-7.78 (m, 2H), 7.70 (dd, J=9.0, 7.3 Hz, 1H).

Workup

  1. stirringstirred for a further 2 hours
  2. customthe layers were partitioned
  3. washThe organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (5-10% methanol in DCM)

Sources & evidence

ORD record
ord-55393755a702465184c54ea1edc404a5
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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