3-Hydrazinylpyridine hydrochloride → 5-(3-Bromo-5-fluorophenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 930011Notes

Reaction equation

HRID 930011 reaction equation
[Li].[Br:2][C:3]1[CH:4]=[C:5]([C:10]([O-])=[CH:11][C:12](=O)[C:13]([O:15]CC)=[O:14])[CH:6]=[C:7]([F:9])[CH:8]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[N:43]1[CH:48]=[CH:47][CH:46]=[C:45]([NH:49][NH2:50])[CH:44]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:10]2[N:49]([C:45]3[CH:44]=[N:43][CH:48]=[CH:47][CH:46]=3)[N:50]=[C:12]([C:13]([OH:15])=[O:14])[CH:11]=2)[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

4

Reactant 3

HCID 231434543-Hydrazinylpyridine hydrochlorideHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131735130Lithium 1-(3-bromo-5-fluorophenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896025905-(3-Bromo-5-fluorophenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

600 mg (1.30 mmol) of the compound of Example 2A is reacted analogously to the synthesis of the compound of Example 20A with 208 mg (1.43 mmol) of 3-pyridylhydrazine hydrochloride. After hydrolysis, 406 mg (86% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-725aff4297ea48938c209565721c60d0
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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