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

HRID 930037Notes

Reaction equation

HRID 930037 reaction equation
[Li].[Cl:2][C:3]1[CH:4]=[C:5]([C:9]([O-])=[CH:10][C:11](=O)[C:12]([O:14]CC)=[O:13])[CH:6]=[N:7][CH:8]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:42][C:43]1[CH:44]=[C:45]([NH:50][NH2:51])[CH:46]=[CH:47][C:48]=1[F:49]>>[Cl:42][C:43]1[CH:44]=[C:45]([N:50]2[C:9]([C:5]3[CH:6]=[N:7][CH:8]=[C:3]([Cl:2])[CH:4]=3)=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[N:51]2)[CH:46]=[CH:47][C:48]=1[F:49]

Participants

4

Reactant 3

HCID 441817773-Chloro-4-fluorophenylhydrazine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735139Lithium 1-(5-chloropyridin-3-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896099741-(3-Chloro-4-fluorophenyl)-5-(5-chloropyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

1.70 g (4.24 mmol) of the compound of Example 14A is reacted analogously to the synthesis of the compound of Example 20A with 1.25 g (6.36 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 896 mg (60% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-b184835a9c5d46c995f14d00f2717e19
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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