Butyl iodide → Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate

HRID 348968

Reaktionsgleichung

Reaktionsgleichung von HRID 348968
[I:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[K+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:18]([N:6]1[C:7]2[C:3](=[C:2]([I:1])[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=2)[CH:4]=[CH:5]1)[CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 14797Potassium HydroxideHCID 851585methyl 4-iodo-1H-indole-6-carboxylate

Produkt 1

HCID 21086136Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of methyl 4-iodo-1H-indole-6-carboxylate (1.0 g) in DMF (10 mL) was added potassium hydroxide (0.392 g) and 1-iodobutane (0.8 mL). The mixture was heated to 80° C. for 18 h. The mixture was cooled to room temperature and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 20% ethyl acetate in hexanes as eluent to give 0.73 g of the title compound: 1H NMR (CDCl3) δ 0.940, 1.32, 1.81, 3.95, 4.15, 6.45, 7.31, 8.09, 8.18.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b85ba07897364fb493119f93cc386d1a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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