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

HRID 2174046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174046
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-caf30f4973174cb2bc36c2116002159a
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

Notizen zur Reaktion

Wird geladen…