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N-bromobutanimide → 3-Bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde

HRID 2174068
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HRID 2174068 반응식
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=[O:23].C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C.O>[Br:31][C:5]1[C:4]2[C:3]([CH:22]=[O:23])=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:11])[C:8]=2[N:7]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 86701532HCID 86701532, 화합물

생성물 1

HCID 867016993-Bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (Example 46-D) (2 g, 6.11 mmol) in DMF (10 mL) was added NBS (2.39 g, 13.44 mmol), and then the mixture was stirred at 60° C. for 18.5 h. The reaction mixture was cooled to room temperature. The mixture was diluted with H2O, the layers were separated and the aqueous layer was extracted with EtOAc. The organic phase was washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel flash column chromatography to give the title compound. MS (ESI+) m/z 406.0, 408.0 (M+H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-b9093bf5ff504153bb1b5294beaa27b0
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056874B2

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