3-Chloro-4-fluorophenylhydrazine hydrochloride → 1-(3-Chloro-4-fluorophenyl)-5-(5-difluoromethoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 930041Notes

Reaction equation

HRID 930041 reaction equation
[Li].[F:2][CH:3]([F:21])[O:4][C:5]1[CH:6]=[C:7]([C:11]([O-])=[CH:12][C:13](=O)[C:14]([O:16]CC)=[O:15])[CH:8]=[N:9][CH:10]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:45][C:46]1[CH:47]=[C:48]([NH:53][NH2:54])[CH:49]=[CH:50][C:51]=1[F:52]>>[Cl:45][C:46]1[CH:47]=[C:48]([N:53]2[C:11]([C:7]3[CH:8]=[N:9][CH:10]=[C:5]([O:4][CH:3]([F:2])[F:21])[CH:6]=3)=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[N:54]2)[CH:49]=[CH:50][C:51]=1[F:52]

Participants

4

Reactant 3

HCID 441817773-Chloro-4-fluorophenylhydrazine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735142Lithium 1-(5-difluoromethoxypyridin-3-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896099601-(3-Chloro-4-fluorophenyl)-5-(5-difluoromethoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

220 mg (0.64 mmol) of the compound of Example 17A is reacted analogously to the synthesis of the compound of Example 20A with 188 mg (0.96 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 120 mg (49% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-45765504f8054b0fb39eee4e8be68b56
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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