5-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acid → HCID 89609968, compound

HRID 930021Notes

Reaction equation

HRID 930021 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.[F: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]([F: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 118006595HCID 118006595, compoundHCID 131734661Lithium 1-(3-bromo-5-trifluoromethoxy phenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 89609968HCID 89609968, compound

Procedure

500 mg (1.16 mmol) of the compound of Example 5A is reacted analogously to the synthesis of the compound of Example 20A with 265 mg (1.62 mmol) of 5-fluoropyridin-3-yl-hydrazine hydrochloride. After hydrolysis, 340 mg (66% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-9ef8da34231145f08bac6e783ca8453e
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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