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

HRID 930036Notes

Reaction equation

HRID 930036 reaction equation
[Li].[F: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]([F: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 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131735138Lithium 1-(5-fluoropyridin-3-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896099591-(3-Chloro-4-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

1.42 g (4.33 mmol) of the compound of Example 13A is reacted analogously to the synthesis of the compound of Example 20A with 1.28 g (6.50 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 854 mg (59% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-ba29dbc9784b4133891784409a653f6b
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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