Triethylborane → 4-[1-Ethyl-4-(4-fluoro-phenyl)-5-trifluoromethyl-1H-pyrazol-3-yl]-benzenesulfonamide

HRID 377694노트

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HRID 377694 반응식
[CH2:1]([N:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:5]([C:19]2[CH:24]=[CH:23][C:22]([S:25](C)(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:4]1)[CH3:2].C([Mg]Cl)CCC.C(B(CC)CC)C.C([O-])(=O)C.[Na+].[NH2:47]OS(O)(=O)=O>C1COCC1.O>[CH2:1]([N:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:5]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH2:47])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:4]1)[CH3:2]

참가 물질

8

반응물 5

HCID 7357TriethylboraneHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 98445471-Ethyl-4-(4-fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-1H-pyrazoleHCID 178418265HCID 178418265, 화합물

생성물 1

HCID 102234614-[1-Ethyl-4-(4-fluoro-phenyl)-5-trifluoromethyl-1H-pyrazol-3-yl]-benzenesulfonamide수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

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온도
25 °C

실험 절차

1-Ethyl-4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole (0.45 g, 1.0 mmol) was dissolved in 5 mL dry THF under nitrogen and treated with 0.9 mL of a 1.0 M solution of n-butyl magnesium chloride in THF at 0° C. for 10 minutes and warmed to 25° C. for 30 minutes. A solution of triethylborane in THF (2.5 mL, 1.0 M) was added and the mixture was stirred at 25° C. for 2 hours and at reflux for 24 hours. After cooling to 25° C., a mixture of water (1.2 mL), sodium acetate (0.90 g) and hydroxylamine-O-sulfonic acid (0.62 g) was added and the reaction stirred at 25° C. for 18 hours. The mixture was partitioned between water and ethyl acetate, and the organic layer washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. Chromatographic purification on silica gel eluting with methyl t-butyl ether/toluene (5/95) gave 4-[1-ethyl-4-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzenesulfonamide as a white solid (0.25 g, 62% yield). Elemental analysis for C18H15N3F4SO2Calc'd: C, 52.30, H, 3.66, N, 10.16, S, 7.76. Found: C, 52.36, H, 3.72, N, 9.98, S, 7.90.

후처리

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling to 25° C.
  3. additionwas added
  4. stirringthe reaction stirred at 25° C. for 18 hours
  5. customThe mixture was partitioned between water and ethyl acetate
  6. washthe organic layer washed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customChromatographic purification on silica gel eluting with methyl t-butyl ether/toluene (5/95)

출처 및 근거

ORD 기록
ord-054b835dd14f46448d38e3f7a5c9503b
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06028072

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