Sodium hydride → 1-(7-Ethoxycarbonylheptyl)-2-(1-imidazolyl)-3-methylindole

HRID 1719389

Reaktionsgleichung

Reaktionsgleichung von HRID 1719389
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O.O.CCOCC>[CH2:29]([O:28][C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[C:3]1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[O:27])[CH3:30]

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 264813Ethyl 8-bromooctanoateHCID 132808392-(1-Imidazolyl)-3-methylindole

Produkt 1

HCID 202681911-(7-Ethoxycarbonylheptyl)-2-(1-imidazolyl)-3-methylindole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

3-Methyl-2-(1-imidazolyl)indole (0.78 g) in dimethylformamide (8 ml) is added dropwise to a suspension of sodium hydride (50% dispersion in mineral oil, 0.20 g) in dimethylformamide (8 ml) stirred under nitrogen at 5°-10°. The resulting solution is stirred at 5°-10° for 1/2 hour. A solution of ethyl 8-bromooctanoate (1.00 g) in dimethylformamide (5 ml) is added dropwise. The reaction mixture is stirred at 5°-10° for 1/2 hour and then overnight at room temperature. The mixture is diluted with water (50 ml) and extracted into methylene chloride (3×25 ml). The extract is washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated in vacuo to give a two-phase oil. This oil is dissolved in ether (50 ml) and the solution is washed with water (5×25 ml) to remove dimethylformamide. The ether layer is dried over MgSO4, filtered, and concentrated in vacuo to give 1-(7-ethoxycarbonylheptyl)-2-(1-imidazolyl)-3-methylindole a viscous oil; NMR (CDCl3): δ 4.12 (q, 2H), 3.82 (t, 2H), 2.20 (s, 3H), 1.23 (t, 3H).

Aufarbeitung

  1. stirringThe resulting solution is stirred at 5°-10° for 1/2 hour
  2. stirringThe reaction mixture is stirred at 5°-10° for 1/2 hour
  3. customovernight
  4. customat room temperature
  5. extractionextracted into methylene chloride (3×25 ml)
  6. washThe extract is washed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a two-phase oil
  11. washthe solution is washed with water (5×25 ml)
  12. customto remove dimethylformamide
  13. dry with materialThe ether layer is dried over MgSO4
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-be37bbef19ba45daad1fdde8f7dd09ba
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539410

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