Chlorosuccinimide → 7-Chloro-5-methyl-1-tosyl-1H-indol-4-amine

HRID 2174046노트

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HRID 2174046 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:21].C1C(=O)N([Cl:29])C(=O)C1>C(#N)C>[Cl:29][C:9]1[C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]([NH2:21])=[C:2]([CH3:1])[CH:10]=1

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 867016685-Methyl-1-tosyl-1H-indol-4-amine

생성물 1

HCID 867016697-Chloro-5-methyl-1-tosyl-1H-indol-4-amine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of 5-methyl-1-tosyl-1H-indol-4-amine (0.52 g, 1.731 mmol) in acetonitrile (17.31 mL) was added NCS (0.231 g, 1.731 mmol), and the mixture was stirred at 50° C. After 2 hours the reaction was cooled to room temperature, quenched with sat. aq. NaHCO3, and with sat. sodium thiosulfate. The layers were separated and the aqueous layer extracted with EtOAc (twice), dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 335.0 (M+H).

후처리

  1. temperatureAfter 2 hours the reaction was cooled to room temperature
  2. customquenched with sat. aq. NaHCO3
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (twice),
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-caf30f4973174cb2bc36c2116002159a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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