Water → 6-Methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,9-dihydro-3H-beta-carboline

HRID 563917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563917
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:15](=O)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1.O=P(Cl)(Cl)Cl.O>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[C:15]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:14][CH2:13][CH2:12][C:6]2=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 59820000N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-3-(4-trifluoromethyl-phenyl)-propionamide

Produkt 1

HCID 1362075296-Methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,9-dihydro-3H-beta-carbolineAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 0.61 g (1.57 mmol) N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-3-(4-trifluoromethyl-phenyl)-propionamide and 1 mL POCl3 in 2.5 mL acetonitrile was heated to reflux for 16 h. Water was added and the mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The combined product fractions were evaporated to dryness to yield 0.09 g (15%) of the title compound as yellow crystals.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. customthe mixture was subjected to purification by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and formic acid
  6. customThe combined product fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7228d24817544f52bb660c76cfc051c3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067598B2

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