3,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile → 4-(7-Bromo-pyrazolo[4,3-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

HRID 626727Notes

Reaction equation

HRID 626727 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:40]([Cl:41])=[CH:39][C:36]([C:37]#[N:38])=[CH:35][C:34]=1[Cl:42])=[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:40]([Cl:41])=[CH:39][C:36]([C:37]#[N:38])=[CH:35][C:34]=3[Cl:42])[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 178509962HCID 178509962, compound

Product 1

HCID 696714484-(7-Bromo-pyrazolo[4,3-c]pyridin-2-yl)-3,5-dichlorobenzonitrileYield 70%

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, 4-{[1-(4-azido-5-bromo-pyridin-3-yl)-meth-(E)-ylidene]-amino}-3,5-dichlorobenzonitrile was heated under reflux in toluene to afford the title compound as a beige solid (3.57 g, 70% yield). 1H NMR (300 MHz, methanol-d4): δ 9.26 (s, 1H), 9.06 (s, 1H), 8.46 (s, 1H), 8.20 (s, 2H).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-777016210478452bb90f949ae93f99ed
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…