4-Bromo-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine → 2-(4-Bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chloro-5-nitrobenzonitrile

HRID 626772Notes

Reaction equation

HRID 626772 reaction equation
[Br:1][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16](Cl)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=3[Cl:21])[N:10]=[C:6]2[C:5]([F:22])=[CH:4][N:3]=1.ClC1C(N2C=C3C(Cl)=NC=C(F)C3=N2)=C(C=C([N+]([O-])=O)C=1)[C:27]#[N:28]>>[Br:1][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:12]([Cl:21])=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][C:16]=3[C:27]#[N:28])[N:10]=[C:6]2[C:5]([F:22])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 866970694-Bromo-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridineHCID 866970713-Chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-5-nitrobenzonitrile

Product 1

HCID 866970702-(4-Bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chloro-5-nitrobenzonitrileYield 83%

Conditions

Temperature
100 °C

Procedure

Following the procedure described for 4-bromo-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine, 3-chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-5-nitrobenzonitrile was heated at 100° C. overnight to afford the title compound as a pale yellow solid (1.38 g, 83% yield). LCMS (Method C): RT=3.62 min, m/z: 396 [M+H+].

Sources & evidence

ORD record
ord-529384bd491f4688a20840bad1179880
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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