2-Bromo-3'-trifluoromethoxyacetophenone → 5-methyl-1-({4-[3-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257320Notes

Reaction equation

HRID 1257320 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]([O:28][C:29]([F:32])([F:31])[F:30])[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]([O:28][C:29]([F:30])([F:31])[F:32])[CH:23]=3)[N:1]=2)[N:5]=[CH:6][C:7]=1[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 27786872-Bromo-3'-trifluoromethoxyacetophenoneHCID 58127752tert-butyl 1-(2-amino-2-thioxoethyl)-5-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 669393415-methyl-1-({4-[3-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acidYield 74.6%

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-(trifluoromethoxy)phenyl]ethanone (222 mg, 0.783 mmol). As a result, the title compound (224 mg, 74%) 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-fc07d6b945d24ffbb9982171bf392d05
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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