Phosphorus oxybromide → 4bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626712Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[N:11]=2)[CH:5]=[N+:6]([O-])[CH:7]=1.P(Br)(Br)([Br:22])=O>ClCCCl>[Br:22][C:5]1[C:4]2=[CH:9][N:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[N:11]=[C:3]2[C:2]([Cl:1])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) suspension of 7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide (2.5 g, 8.0 mmol) in DCE (50 mL) was added phosphorus oxybromide (6.8 g, 24.0 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, warmed to room temperature, and stirred for a further 18 hours. The reaction mixture was partitioned between DCM and sodium carbonate (sat. aq.). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as a white solid (850 mg, 28% yield). LCMS (Method D): RT=3.92 min, m/z: 377 [M+H+].

Workup

temperatureTo a cooled
temperaturewarmed to room temperature
stirringstirred for a further 18 hours
customThe reaction mixture was partitioned between DCM and sodium carbonate (sat. aq.)
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-8dcf5c73ec7d463f8f72b83bc7f58d31
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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