2-Chloro-4-hydrazinylpyridine hydrochloride → 5-(3-Bromo-5-methoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

HRID 930028Notes

Reaction equation

HRID 930028 reaction equation
[Li].[Br:2][C:3]1[CH:4]=[C:5]([C:11]([O-])=[CH:12][C:13](=O)[C:14]([O:16]CC)=[O:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:44][C:45]1[CH:50]=[C:49]([NH:51][NH2:52])[CH:48]=[CH:47][N:46]=1>>[Br:2][C:3]1[CH:4]=[C:5]([C:11]2[N:51]([C:49]3[CH:48]=[CH:47][N:46]=[C:45]([Cl:44])[CH:50]=3)[N:52]=[C:13]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

4

Reactant 3

HCID 865938392-Chloro-4-hydrazinylpyridine hydrochlorideHCID 89602575HCID 89602575, compoundHCID 131735132Lithium 1-(3-bromo-5-methoxyphenyl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896024725-(3-Bromo-5-methoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Procedure

500 mg (1.19 mmol) of the compound of Example 6A is reacted analogously to the synthesis of the compound of Example 20A with 322 mg (1.79 mmol) of 2-chloropyridin-4-yl-hydrazine hydrochloride. After hydrolysis, 259 mg (53% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-3b91cddfafe249ac845f1fccb4f483a8
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

Loading…