Methyl iodide → Methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245165

Reaktionsgleichung

Reaktionsgleichung von HRID 245165
[H-].[Na+].F[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([OH:29])=[O:28].[CH2:30]([S-:32])[CH3:31].[Na+].I[CH3:35]>CS(C)=O.O>[CH2:30]([S:32][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([O:29][CH3:35])=[O:28])[CH3:31]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4459711Sodium ethanethiolateHCID 673840026-Fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Produkt 1

HCID 67418873Methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (1.27 g, 31.6 mmol) was added portionwise to a suspension of 6-fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (8.0 g, 21.09 mmol) in dimethyl sulfoxide (50 mL). The mixture was stirred for 20 min. Sodium ethanethiolate (2.168 g, 23.20 mmol) was added and the resulting mixture was stirred at 100° C. for 1 h. The mixture was cooled to room temperature, iodomethane (3.96 mL, 63.3 mmol) was added, and the mixture was stirred for 2 h. The reaction mixture was diluted with water and was extracted with methylene chloride (three times). The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 330 g silica, 0-10% ethyl acetate/methylene chloride) to afford methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (7.05 g, 77% yield, about 70% pure). MS (m/z) 436.1 (M+H+).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 100° C. for 1 h
  2. stirringthe mixture was stirred for 2 h
  3. extractionwas extracted with methylene chloride (three times)
  4. washThe combined organic extracts were washed with brine (two times)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via column chromatography (ISCO, 330 g silica, 0-10% ethyl acetate/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-ec3dc2ef18b144b58fe16e13a12ecbe5
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

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