5-(Oct-1-ynyl)-1H-indole → 5-octyl-1H-indole

HRID 710287

Reaktionsgleichung

Reaktionsgleichung von HRID 710287
[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CCO.[Pd].[C]>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

4

Edukt 1

HCID 667267515-(Oct-1-ynyl)-1H-indole

Produkt 1

HCID 667262575-octyl-1H-indoleAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of the product of Step A (0.17 g; 0.75 mmol) and 10% Pd/carbon (0.2 g) in EtOH (15 ml) was stirred at room temperature for 40 min under H2 (balloon). The catalyst was removed by filtration through the Celite pad, washed with CH2Cl2 (2×10 ml) and combined filtrates were evaporated to dryness under reduced pressure. The residue was purified by FCC (SiO2; hexane/EtOAc; 9:1) to give the title compound (0.08 g; 46%) as a colourless syrup. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.7 Hz); 1.28 (m, 10H); 1.65 (m, 2H); 2.68 (tr, 2H, J=7.9 Hz); 6.47 (m, 1H); 7.02 (dd, 1H, J=1.5, 8.3 Hz); 7.16 (m, 1H); 7.29 (d, 1H, J=8.3 Hz); 7.42 (s, 1H); 8.04 (broad s, 1H).

Aufarbeitung

  1. customThe catalyst was removed by filtration through the Celite pad
  2. washwashed with CH2Cl2 (2×10 ml)
  3. customwere evaporated to dryness under reduced pressure
  4. customThe residue was purified by FCC (SiO2; hexane/EtOAc; 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d6ac4178d54e45dc807d3c7923865d7a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

Verknüpfte Notizen

Wird geladen…