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

HRID 1251791노트

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HRID 1251791 반응식
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

참가 물질

4

반응물 2

HCID 25953Cesium fluorideHCID 22998524HCID 22998524, 화합물

생성물 1

HCID 22998493N-(3,4-dimethyl-5-isoxazolyl)-2-(alpha-hydroxybenzyl)thiophene-3-sulfonamide수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)-2-(α-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-(α-hydroxybenzyl)thiophene-3-sulfonamide as a pale white semisolid (51% yield).

후처리

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

출처 및 근거

ORD 기록
ord-879eba9c82ac47e3981a1911088fc900
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06342610B2

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