2-Chloro-6-hydrazinopyridine → 5-(3-Bromo-5-trifluoromethoxyphenyl)-1-(6-chloropyridin-2-yl)-1H-pyrazole-3-carboxylic acid

HRID 930015Notes

Reaction equation

HRID 930015 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:46][C:47]1[N:52]=[C:51]([NH:53][NH2:54])[CH:50]=[CH:49][CH:48]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:14]2[N:53]([C:51]3[CH:50]=[CH:49][CH:48]=[C:47]([Cl:46])[N:52]=3)[N:54]=[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 3200042-Chloro-6-hydrazinopyridineHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131734661HCID 131734661, compound

Product 1

HCID 896099565-(3-Bromo-5-trifluoromethoxyphenyl)-1-(6-chloropyridin-2-yl)-1H-pyrazole-3-carboxylic acid

Procedure

1.10 g (2.40 mmol) of the compound of Example 5A is reacted analogously to the synthesis of the compound of Example 20A with 518 mg (3.61 mmol) of 6-chloropyridin-2-yl-hydrazine. After hydrolysis, 737 mg (66% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-0feb8f71fea84293befd8e0c884d4c05
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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