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

HRID 2174046ノート

反応式

HRID 2174046 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-caf30f4973174cb2bc36c2116002159a
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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