Potassium Fluoride → methyl 4-[1-methyl-4-(trifluoromethyl)-1H-pyrazol-5-yl]-2-thiophenecarboxylate

HRID 2392277Notes

Reaction equation

I[C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=1.[F-].[K+].C([Si](CC)(CC)[C:22]([F:25])([F:24])[F:23])C>CN(C=O)C.CN(P(N(C)C)(N(C)C)=O)C.[Cu]I>[CH3:16][N:5]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=2)=[C:2]([C:22]([F:25])([F:24])[F:23])[CH:3]=[N:4]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 4-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (470 mg, 1.35 mmol), copper (I) iodide (256 mg, 1.35 mmol) and potassium fluoride (78 mg, 1.35 mmol) in anhydrous DMF/HMPA (2 ml/2 mL) was added triethyl(trifluoromethyl)silane (745 mg, 4.04 mmol). The mixture was heated to 70° C. under N2 in a sealed tube. After 10 h, the reaction was quenched with NH4Cl (sat'd) (2 mL), extracted with ether (5 mL×5) and washed with distilled water (5 mL×5). The combined organic phase was dried over Mg2SO4 and purified on silica (EtOAc/Hex, 10-30%) to afford the title compound (0.29 g, 74%) as a yellow syrup: LC-MS (ES) m/z 291 (M+H)+.

Workup

customthe reaction was quenched with NH4Cl (sat'd) (2 mL)
extractionextracted with ether (5 mL×5)
washwashed with distilled water (5 mL×5)
dry with materialThe combined organic phase was dried over Mg2SO4
custompurified on silica (EtOAc/Hex, 10-30%)

Sources & evidence

ORD record: ord-54bd122666b047eebf8aeb0994ec8589
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273782B2

Reaction notes

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