3,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile → 7-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626730Notes

Reaction equation

HRID 626730 reaction equation
ClC1C=C(C=C(Cl)C=1N1C=C2C=NC=C(Cl)C2=N1)C#N.[N:21]([C:24]1[C:29]([Br:30])=[CH:28][N:27]=[CH:26][C:25]=1/[CH:31]=[N:32]/[C:33]1[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:40])=[N+]=[N-]>C1(C)C=CC=CC=1>[Br:30][C:29]1[C:24]2[C:25](=[CH:31][N:32]([C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])[N:21]=2)[CH:26]=[N:27][CH:28]=1

Participants

4

Reactant 2

HCID 696716223,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrileHCID 178514475HCID 178514475, compound

Product 1

HCID 696713917-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure described for 3,5-dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile, [1-(4-azido-5-bromopyridin-3-yl)-meth-(E)-ylidene]-(2,6-dichlorophenyl)-amine was heated under reflux in toluene to afford the title compound as a brown solid (7.5 g, 81% yield). LCMS (Method D): RT=2.90 min, m/z: 344 [M+H+].

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-f817dc899dfc424cb8b2f29523dc83c5
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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