5-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acid → 5-(3-Bromo-5-trifluoromethoxyphenyl)-1-(2-trifluoromethylpyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930024Notes

Reaction equation

HRID 930024 reaction equation
[Li].[Br:2][C:3]1[CH:4]=[C:5]([C:14]([O-])=[CH:15][C:16](=O)[C:17]([O:19]CC)=[O:18])[CH:6]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:8]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[F:47][C:48]([F:58])([F:57])[C:49]1[CH:54]=[C:53]([NH:55][NH2:56])[CH:52]=[CH:51][N:50]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:14]2[N:55]([C:53]3[CH:52]=[CH:51][N:50]=[C:49]([C:48]([F:47])([F:57])[F:58])[CH:54]=3)[N:56]=[C:16]([C:17]([OH:19])=[O:18])[CH:15]=2)[CH:6]=[C:7]([O:9][C:10]([F:11])([F:12])[F:13])[CH:8]=1

Participants

4

Reactant 3

HCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 1180065252-Trifluoromethylpyridin-4-yl-hydrazine hydrochlorideHCID 131734661HCID 131734661, compound

Product 1

HCID 896100545-(3-Bromo-5-trifluoromethoxyphenyl)-1-(2-trifluoromethylpyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

500 mg (1.16 mmol) of the compound of Example 5A is reacted analogously to the synthesis of the compound of Example 20A with 370 mg (1.74 mmol) of 2-trifluoromethylpyridin-4-yl-hydrazine hydrochloride. After hydrolysis, 307 mg (53% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-f855a86b2cb34b1e989114273445f580
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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