Water → trans-Ethyl 2-(5-fluoro-2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate

HRID 1639782노트

반응식

HRID 1639782 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CS(C)=O>[F:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1[C@@H:20]1[CH2:4][C@H:21]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720771ethyl (2E)-3-(5-fluoro-2-methyl-2H-indazol-4-yl)acrylate

생성물 1

HCID 131729435trans-Ethyl 2-(5-fluoro-2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate수율 46.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

실험 절차

To a suspension of sodium hydride (0.793 g, 18.2 mmol) in dimethyl sulfoxide (100 mL) was added a solution of trimethylsulfoxonium iodide (4.00 g, 18.2 mmol) in dimethyl sulfoxide (100 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl (2E)-3-(5-fluoro-2-methyl-2H-indazol-4-yl)acrylate (4.10 g, 16.5 mmol) in dimethyl sulfoxide (130 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (2.00 g, yield 46%).

후처리

  1. stirringthe mixture was stirred at room temperature for 14 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3)

출처 및 근거

ORD 기록
ord-01782f96316946ada08ba4c177148789
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110585B2

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