2-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one → 5-methyl-1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257321Notes

Reaction equation

HRID 1257321 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][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)=O>>[CH3:9][C:8]1[N:4]([CH2:3][C:2]2[S:17][CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[N:1]=2)[N:5]=[CH:6][C:7]=1[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-oneHCID 58127752tert-butyl 1-(2-amino-2-thioxoethyl)-5-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 669389085-methyl-1-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acidYield 81.7%

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-(trifluoromethyl)phenyl]ethanone (209 mg, 0.783 mmol). As a result, the title compound (235 mg, 81%) 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-7ef20191e7a54b47931671a4f5e4ff29
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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