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

HRID 930042Notes

Reaction equation

HRID 930042 reaction equation
[Li].[F:2][C:3]([F:22])([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:46][C:47]1[CH:48]=[C:49]([NH:54][NH2:55])[CH:50]=[CH:51][C:52]=1[F:53]>>[Cl:46][C:47]1[CH:48]=[C:49]([N:54]2[C:11]([C:7]3[CH:8]=[N:9][CH:10]=[C:5]([O:4][C:3]([F:2])([F:21])[F:22])[CH:6]=3)=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[N:55]2)[CH:50]=[CH:51][C:52]=1[F:53]

Participants

4

Reactant 3

HCID 441817773-Chloro-4-fluorophenylhydrazine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735143Lithium 1-(5-trifluoromethoxypyridin-3-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896099791-(3-Chloro-4-fluorophenyl)-5-(5-trifluoromethoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

1.13 g (3.25 mmol) of the compound of Example 18A is reacted analogously to the synthesis of the compound of Example 20A with 961 mg (4.88 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 576 mg (44% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-14f5c63508034cc1a8062fca29ab9ddf
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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