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

HRID 626743Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:19]=[C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:18])[C:12]2=[N:11]1.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:19]=[C:13]2[CH:14]=[N+:15]([O-:28])[CH:16]=[C:17]([F:18])[C:12]2=[N:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 2-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (3.37 g, 11.2 mmol) in DCM (50 mL) under nitrogen, was added mCPBA (2.9 g, 16.8 mmol). The reaction mixture was stirred at 0° C. for 2 hours, warmed to room temperature, and stirred for a further 5 hours. The reaction was washed with sodium thiosulfate (sat. aq.), sodium hydrogen carbonate (sat. aq.), and brine. The organic layer was then dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by trituration with diethyl ether to afford the title compound as an off-white solid (2.98 g, 84% yield). LCMS (Method D): RT=2.48 min, m/z: 316 [M+H+].

Workup

temperaturewarmed to room temperature
stirringstirred for a further 5 hours
washThe reaction was washed with sodium thiosulfate (sat. aq.), sodium hydrogen carbonate (sat. aq.), and brine
dry with materialThe organic layer was then dried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by trituration with diethyl ether

Sources & evidence

ORD record: ord-a9aaa562948041c4b8e55cfd55092194
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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