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

HRID 68158

반응식

HRID 68158 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 58492496methyl 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionate수율 75.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ae0d3f04578741a88bffe5a0a1aebf30
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045108E1

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