Potassium Iodide → 2-Ethyl-6-fluoro-3-{1-[3-(4-fluoro-phenylsulfanyl)-propyl]-piperidin-4-yl}-1H-indole

HRID 2356387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356387
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2].Br[CH2:20][CH2:21][CH2:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:20][CH2:21][CH2:22][S:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2]

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14575314Benzene, 1-[(3-bromopropyl)thio]-4-fluoro-HCID 577188362-Ethyl-6-fluoro-3-piperidin-4-yl-1H-indole

Produkt 1

HCID 577188372-Ethyl-6-fluoro-3-{1-[3-(4-fluoro-phenylsulfanyl)-propyl]-piperidin-4-yl}-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole (0.9 g), 1-(3-Bromo-propylsulfanyl)-4-fluoro-benzene (1.0 g), potassium iodide (20 mg) and potassium carbonate (0.7 g) in DMF (10 ml) is heated at 100° C. for 3 h, and allowed to cool to rt overnight. Ethyl acetate (50 ml) and water (25 ml) are added and the organic phase is washed with water, dried and concentrated in vacuo. The crude product is purified by flash chromatography (95:5 CH2Cl2:MeOH) and its hydrochloride salt is prepared by reaction in acetone with the appropriate amount of ethereal HCl giving, after recrystallisation from ether, 1.1 g pure product (70%) as white crystals.

Aufarbeitung

  1. temperatureto cool to rt overnight
  2. washthe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography (95:5 CH2Cl2:MeOH) and its hydrochloride salt
  6. customis prepared by reaction in acetone with the appropriate amount of ethereal HCl giving
  7. customafter recrystallisation from ether, 1.1 g pure product (70%) as white crystals

Quellen und Nachweise

ORD-Eintrag
ord-81d413e111dd46c4a5cd7d679dfd1885
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759365B2

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