Butyl iodide → methyl 1-butyl-1H-indole-6-carboxylate

HRID 14221

Reaktionsgleichung

Reaktionsgleichung von HRID 14221
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].I[CH2:21][CH2:22][CH2:23][CH3:24]>CS(C)=O>[CH2:21]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1)[CH2:22][CH2:23][CH3:24]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 639844Methyl indole-6-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 21086134methyl 1-butyl-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Methyl 1H-indole-6-carboxylate (4.17 g) was dissolved in DMSO (30 mL), and potassium tert-butoxide (2.93 g) was added. The mixture was stirred for ten min at room temperature. Iodobutane (3.0 mL) was added. The mixture was allowed to stir for three additional hours. The mixture was partitioned between ethyl acetate and water and brine, dried over sodium sulfate, filtered, and concentrated to give methyl 1-butyl-1H-indole-6-carboxylate (4.53 g). MS (ESI+) for C14H17NO2+H1 m/z 232.12 (M+H)+.

Aufarbeitung

  1. stirringto stir for three additional hours
  2. customThe mixture was partitioned between ethyl acetate and water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-986f12927c2143d6a3c663c2a48c33dd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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