Cesium fluoride → N-(3,4-dimethyl-5-isoxazolyl)-2-(alpha-hydroxybenzyl)thiophene-3-sulfonamide

HRID 2270720Notes

Reaction equation

C[Si](C)(C)CCOC[C:7]1([CH:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:11]([S:12]([NH:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[C:17]=2[CH3:22])(=[O:14])=[O:13])[CH:10]=[CH:9][S:8]1.[F-].[Cs+]>CN(C=O)C>[CH3:21][C:18]1[C:17]([CH3:22])=[C:16]([NH:15][S:12]([C:11]2[CH:10]=[CH:9][S:8][C:7]=2[CH:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:14])=[O:13])[O:20][N:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)-2-(a-hydroxybenzyl)thiophene-3-sulfonamide (70 mg, 0-14 mmol) in DMF (2 ml) was added cesium fluoride (26 mg, 0.17 mmole) in one portion. The resulting mixture was heated to 100° C. for 10 hours. The solvents were removed by evaporation under vacuum and the remaining residue was extracted into ethyl acetate, washed with water, brine, and dried over MgSO4. The product was then purified by chromatography using 50-70% ethyl acetate/hexanes to give 26.2 mg N-(3,4-dimethyl-5-isoxazolyl)-2-(a-hydroxybenzyl)thiophene-3-sulfonamide as a pale white semisolid (51% yield).

Workup

customThe solvents were removed by evaporation under vacuum
extractionthe remaining residue was extracted into ethyl acetate
washwashed with water, brine
dry with materialdried over MgSO4
customThe product was then purified by chromatography

Sources & evidence

ORD record: ord-c72e87c3599d43e0b9389784777a2463
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331637B1

Reaction notes

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