2-Chloro-4-hydrazinylpyridine hydrochloride → 5-(3-Bromo-5-trifluoromethoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930023Notes

Reaction equation

HRID 930023 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.[Cl:47][C:48]1[CH:53]=[C:52]([NH:54][NH2:55])[CH:51]=[CH:50][N:49]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:14]2[N:54]([C:52]3[CH:51]=[CH:50][N:49]=[C:48]([Cl:47])[CH:53]=3)[N:55]=[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 865938392-Chloro-4-hydrazinylpyridine hydrochlorideHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131734661HCID 131734661, compound

Product 1

HCID 896100585-(3-Bromo-5-trifluoromethoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

690 mg (1.77 mmol) of the compound of Example 5A is reacted analogously to the synthesis of the compound of Example 20A with 350 mg (1.94 mmol) of 2-chloropyridin-4-yl-hydrazine hydrochloride. After hydrolysis, 475 mg (58% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-7f121d7795fe4eafb8c23423837cd186
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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