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

HRID 626675Notes

Reaction equation

HRID 626675 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]([F: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]([F: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 696716312-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 696711682-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (2.38 g, 13.88 mmol) was added to a cooled 0° C.) solution of 2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (2.27 g, 9.2 mmol) in DCM (55 mL) under nitrogen. The reaction was stirred for 3 hours, warmed to room temperature, and stirred for an additional 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 under reduced pressure. The residue was purified by silica gel flash chromatography (5-10% methanol in DCM) to afford the title compound as a beige solid (2.13 g, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.90 (dd, J=1.8, 0.9 Hz, 1H), 8.87 (s, 1H), 7.95 (dd, J=7.5, 1.8 Hz, 1H), 7.83 (dt, J=7.5, 1.0 Hz, 1H), 7.74 (td, J=8.3, 5.8 Hz, 1H), 7.65-7.63 (m, 2H).

Workup

  1. stirringstirred for an additional 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 under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (5-10% methanol in DCM)

Sources & evidence

ORD record
ord-17f6105aa20d49019d78817ec19a685f
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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