2-Bromo-1-(3,4-dichlorophenyl)ethanone → 1-{[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]methyl}-5-methyl-1H-pyrazole-4-carboxylic acid

HRID 1257319Notes

Reaction equation

HRID 1257319 reaction equation
[NH2:1][C:2](=[S:17])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([O:12]C(C)(C)C)=[O:11])[CH:6]=[N:5]1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)=O>>[Cl:29][C:24]1[CH:23]=[C:22]([C:20]2[N:1]=[C:2]([CH2:3][N:4]3[C:8]([CH3:9])=[C:7]([C:10]([OH:12])=[O:11])[CH:6]=[N:5]3)[S:17][CH:19]=2)[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

3

Reactant 2

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 58127752tert-butyl 1-(2-amino-2-thioxoethyl)-5-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 581279501-{[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]methyl}-5-methyl-1H-pyrazole-4-carboxylic acidYield 79.8%

Procedure

A reaction similar to Example 1c was performed using the compound (200 mg, 0.783 mmol) obtained in Example 11b and 2-bromo-1-(3,4-dichlorophenyl)ethanone (210 mg, 0.783 mmol). As a result, the title compound (230 mg, 79%) wherein tert-butyl ester was hydrolyzed by hydrobromic acid produced under the reaction conditions was obtained as colorless crystals.

Workup

  1. customA reaction similar to Example 1c

Sources & evidence

ORD record
ord-910794d66325405b84d8355860e496c4
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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