Citric Acid → 2-bromo-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide

HRID 1357102

반응식

HRID 1357102 반응식
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([Mg]Br)C.[Br:15][C:16]1[C:17]([N:19]([CH3:24])[C:20](=[O:23])[C:21]=1Br)=[O:18].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Br:15][C:16]1[C:17]([N:19]([CH3:24])[C:20](=[O:23])[C:21]=1[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[NH:7][CH:6]=1)=[O:18]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 119785-MethylindoleHCID 181552,3-Dibromo-N-methylmaleimideHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 98835102-bromo-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide수율 86.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
40 °C

실험 절차

To a solution of 5-methylindole (90 mg, 0.78 mmol) dissolved in THF (3 mL) was added 0.95M ethylmagnesium bromide (0.83 mL, 0.78 mmol) at 40° C., and the whole was stirred at 40° C. for 45 minutes. Successively, thereto was added a solution of 2,3-dibromo-N-methylmaleimide (100 mg, 0.39 mmol) dissolved in THF (5 mL), followed by stirring under heating and refluxing for 3 hours. After 20% aqueous citric acid solution (1 mL) was added thereto under ice cooling and the whole was stirred, THF was removed by concentration under reduced pressure and the resulting concentrate was extracted with ethyl acetate. The extract was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=1:1) to obtain 2-bromo-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide (108 mg, 86.3%) as red solids.

후처리

  1. stirringby stirring
  2. temperatureunder heating
  3. temperaturerefluxing for 3 hours
  4. stirringunder ice cooling and the whole was stirred
  5. customTHF was removed by concentration under reduced pressure
  6. concentrationthe resulting concentrate
  7. extractionwas extracted with ethyl acetate
  8. dry with materialThe extract was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-ee1861e7df8a4453a81ee0ed5030694f
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589977B1

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