Reaction #155340

Reaction equation

1-(2-Chloroethyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

methyl 3-mercaptopropionate

sodium iodide

DMF

→

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

Yield 75.2%

Solvents

ethyl acetate

Water

Conditions

Workup

1. 1
   Otherfollowed by separation
2. 2
   WashThe thus-obtained organic layer was washed with water
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue was purified
6. 6
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

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%).

Source