Sodium Trifluoroacetate → HCID 19965114, compound

HRID 977107Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].[F:24][C:25]([F:30])([F:29])C([O-])=O.[Na+]>CN1CCCC1=O>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([CH3:18])[N:17]=2)=[CH:3][C:2]=1[C:25]([F:30])([F:29])[F:24])[CH:10]([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 140 °C

Procedure

100 mg of Ethyl 2-(3-bromo-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylate, 95 mg of cuprous iodide and 140 mg of sodium trifluoroacetate were suspended in 2 ml of N-methylpyrrolidone, and the mixture was heated in a nitrogen atmosphere at 140° C. for 4 hours. After completion of the reaction, the product was extracted with ethyl acetate, and the organic layer was concentrated to give a crude crystal. The resulting crystal was purified by silica gel chromatography to give 80 mg of ethyl 2-(4-isobutyloxy-3-trifluoromethylphenyl)-4-methyl-5-thiazolecarboxylate. The product was hydrolyzed by a conventional process, following by recrystallization from hexane-ether to give 50 mg of 2-(4-isobutyloxy-3-trifluomethylphenyl)-4-methyl-5-thiazolecarboxylic acid (yield: 56%).

Workup

customAfter completion of the reaction
extractionthe product was extracted with ethyl acetate
concentrationthe organic layer was concentrated
customto give a crude crystal
customThe resulting crystal was purified by silica gel chromatography

Sources & evidence

ORD record: ord-73dcf984c603473882f15e85179a098b
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614520

Reaction notes

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