2-Chloro-4-hydrazinylpyridine hydrochloride → 5-(3-Bromo-5-fluorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930012Notes

Reaction equation

HRID 930012 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.[Cl:43][C:44]1[CH:49]=[C:48]([NH:50][NH2:51])[CH:47]=[CH:46][N:45]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:10]2[N:50]([C:48]3[CH:47]=[CH:46][N:45]=[C:44]([Cl:43])[CH:49]=3)[N:51]=[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 865938392-Chloro-4-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 896100015-(3-Bromo-5-fluorophenyl)-1-(2-chloropyridin-4-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 257 mg (1.43 mmol) of 2-chloropyridin-4-yl-hydrazine hydrochloride. After hydrolysis, 175 mg (34% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-d3437cc0a3804ce3bd6bc5a4859649ea
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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