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

HRID 930027Notes

Reaction equation

HRID 930027 reaction equation
[Li].[Br:2][C:3]1[CH:4]=[C:5]([C:11]([O-])=[CH:12][C:13](=O)[C:14]([O:16]CC)=[O:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([NH:50][NH2:51])[CH:45]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:11]2[N:50]([C:46]3[CH:45]=[N:44][CH:49]=[CH:48][CH:47]=3)[N:51]=[C:13]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[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 131735132Lithium 1-(3-bromo-5-methoxyphenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896025285-(3-Bromo-5-methoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

500 mg (1.19 mmol) of the compound of Example 6A is reacted analogously to the synthesis of the compound of Example 20A with 260 mg (1.79 mmol) of 3-pyridylhydrazine hydrochloride. After hydrolysis, 240 mg (54% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-ddf662de55ce465eaaabbfe474c3aa32
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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