Water → 6-Bromo-1-(3-methoxypropyl)-1H-indole

HRID 252339

Reaktionsgleichung

Reaktionsgleichung von HRID 252339
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:14][CH2:15][CH2:16][O:17][CH3:18].O>CN1C(=O)N(C)CCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1189271-Chloro-3-methoxypropaneHCID 6764936-Bromoindole

Produkt 1

HCID 231516746-Bromo-1-(3-methoxypropyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

The stirred solution of 25 g of 6-bromo-1H-indole [52415-29-9] in 250 ml of DMPU is admixed at 0° C. with 11.2 g of sodium hydride (60% in mineral oil) in portions. The mixture is stirred over 1 hour and then admixed with 60.9 g of 1-chloro-3-methoxypropane and 4.71 g of tetrabutylammonium iodide (exothermic reaction). The mixture is stirred at room temperature over a further 1 hour. The resulting reaction mixture is poured onto 2 l of water (cold) and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water (3×) and brine, dried over sodium sulphate and filtered, and the filtrate is concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.31 (1:2 EtOAc-heptane). Rt=5.10 (gradient I).

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature over a further 1 hour
  2. customThe resulting reaction mixture
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed successively with water (3×) and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-42a46c7ffb3e47b4bddaa7ddde6dc90d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868036B2

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