Sodium Iodide → methyl 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionate

HRID 68158

Reaktionsgleichung

Reaktionsgleichung von HRID 68158
Cl[CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[C:9]([F:18])[CH:10]=[CH:11][C:12]=2[O:14][CH2:15][CH2:16][CH3:17])[C:7](=[O:19])[C:6]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:5]1.[SH:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].[I-].[Na+].CN(C=O)C>C(OCC)(=O)C.O>[F:18][C:9]1[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH2:16][CH3:17])=[C:13]2[C:8]=1[C:7](=[O:19])[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[CH:5][N:4]2[CH2:3][CH2:2][S:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 18050Methyl 3-mercaptopropionateHCID 584925571-(2-Chloroethyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Produkt 1

HCID 58492496methyl 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-(2-Chloroethyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (3.5 g, 8.98 mmol), methyl 3-mercaptopropionate (1.19 g, 9.88 mmol), and sodium iodide (1.48 g, 9.88 mmol) were added to DMF (30 ml) and stirred at 80° C. for 5 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane). The purified product was concentrated to dryness under reduced pressure, giving a pale yellow powder of methyl 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionate (3.2 g, yield: 75%).

Aufarbeitung

  1. customfollowed by separation
  2. washThe thus-obtained organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. concentrationThe purified product was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae0d3f04578741a88bffe5a0a1aebf30
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045108E1

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