5-Hydrazinyl-2-methylpyridine--hydrogen chloride (1/1) → 5-(3-Bromo-5-trifluoromethoxyphenyl)-1-(6-methylpyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 930018Notes

Reaction equation

HRID 930018 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.[CH3:47][C:48]1[N:53]=[CH:52][C:51]([NH:54][NH2:55])=[CH:50][CH:49]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:14]2[N:54]([C:51]3[CH:52]=[N:53][C:48]([CH3:47])=[CH:49][CH:50]=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 248205115-Hydrazinyl-2-methylpyridine--hydrogen chloride (1/1)HCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131734661HCID 131734661, compound

Product 1

HCID 896025395-(3-Bromo-5-trifluoromethoxyphenyl)-1-(6-methylpyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

656 g (1.35 mmol) of the compound of Example 5A is reacted analogously to the synthesis of the compound of Example 20A with 359 mg (2.02 mmol) of 6-methylpyridin-3-yl-hydrazine hydrochloride. After hydrolysis, 53 mg (9% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-9f78b751e83a468aac75f1e89c331efa
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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