Trifluoroacetic acid → 5-Methyl-1-tosyl-1H-indol-4-amine

HRID 2174045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174045
[CH3:1][C:2]1[C:3]([NH:21]C(=O)OC(C)(C)C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86701666tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate (10.5 g, 26.2 mmol) in DCM (197 mL) was added TFA (65.5 mL), and the mixture was stirred at room temperature. After 20 minutes the reaction was concentrated, dissolved in EtOAc, washed with sat. aq. NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 301.1 (M+H).

Aufarbeitung

  1. concentrationAfter 20 minutes the reaction was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-d1969f0c74b444ce9fe0f24b4e33138b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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