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

HRID 68158

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

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%).

Workup

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

Sources & evidence

ORD record: ord-ae0d3f04578741a88bffe5a0a1aebf30
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE045108E1

Linked notes

Loading…