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Iodoethane → N-[3-(4-bromo-1-ethyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide

HRID 45898
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HRID 45898 반응식
[Br:1][C:2]1[C:3]([C:7]2[C:8]([F:32])=[C:9]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=2[F:13])=[N:4][NH:5][CH:6]=1.[OH-].[Na+].[CH2:35](I)[CH3:36]>C(Cl)Cl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[Br:1][C:2]1[C:3]([C:7]2[C:8]([F:32])=[C:9]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=2[F:13])=[N:4][N:5]([CH2:35][CH3:36])[CH:6]=1.[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH2:35][CH3:36])[C:3]=1[C:7]1[C:8]([F:32])=[C:9]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=1[F:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 178496268HCID 178496268, 화합물

생성물 2

HCID 67183880N-[3-(4-bromo-1-ethyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide수율 50%HCID 67185634N-[3-(4-bromo-2-ethyl-2H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide
수율 26%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매2회

실험 절차

N-[3-(4-bromo-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide (584 mg, 1.085 mmol) was dissolved in DCM (5 mL). 32% sodium hydroxide was added (5 mL) followed by ethyl iodide (0.13 mL, 1.628 mmol, 1.5 eq) and TBAB (58 mg, 0.18 mmol, 0.17 eq) and the biphasic mixture was vigorously stirred at room temperature for 3 hours. The reaction mixture was then diluted with DCM, washed with water and brine, dried over Na2SO4 and evaporated to dryness. The two ethyl pyrazole regioisomers have been separated by chromatography on silica gel (n-hexane/ethyl acetate 7:3): 308 mg (50% yield) of the desired regioisomer N-[3-(4-bromo-1-ethyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide were obtained along with 160 mg (26% yield) of the minor regioisomer N-[3-(4-bromo-2-ethyl-2H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe two ethyl pyrazole regioisomers have been separated by chromatography on silica gel (n-hexane/ethyl acetate 7:3)

출처 및 근거

ORD 기록
ord-8fed6ec6877c4066ae8d657809d139c9
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541575B2

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