4-Hydrazino-2-methylpyridine hydrobromide → 5-(3-Bromo-5-trifluoromethoxyphenyl)-1-(2-methylpyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930025Notes

Reaction equation

HRID 930025 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.Br.[CH3:47][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]([CH3:47])[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 509994494-Hydrazino-2-methylpyridine hydrobromideHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131734661HCID 131734661, compound

Product 1

HCID 896099325-(3-Bromo-5-trifluoromethoxyphenyl)-1-(2-methylpyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

500 mg (1.03 mmol) of the compound of Example 5A is reacted analogously to the synthesis of the compound of Example 20A with 315 mg (1.54 mmol) of 2-methylpyridin-4-yl-hydrazine hydrobromide. After hydrolysis, 182 mg (40% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-2a2d2f57eb3a48f2a8b1e8f7d7a721de
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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