5-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acid → HCID 89610002, compound

HRID 930020Notes

Reaction equation

HRID 930020 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:49]=[C:50]([NH:54][NH2:55])[CH:51]=[N:52][CH:53]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:14]2[N:54]([C:50]3[CH:51]=[N:52][CH:53]=[C:48]([Cl:47])[CH:49]=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 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 118006407HCID 118006407, compoundHCID 131734661Lithium 1-(3-bromo-5-trifluoromethoxy phenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 89610002HCID 89610002, compound

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 364 mg (2.02 mmol) of 5-chloropyridin-3-yl-hydrazine hydrochloride. After hydrolysis, 278 mg (45% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-c85f7e34c06a461ca98fbe5cc9551589
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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