(3-Amino-4-fluorophenoxy)acetic acid methyl ester → [2-ethyl-8-fluoro-3-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic Acid Methyl Ester
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH2:13])[CH:7]=1.C[O:16][C:17](=O)[CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:19](=O)[CH2:20][CH3:21]>O1CCOCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:7]=1[C:17](=[O:16])[C:18]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)=[C:19]([CH2:20][CH3:21])[NH:13]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of (3-amino-4-fluorophenoxy)acetic acid methyl ester (0.80 g), 2-(4-fluorobenzyl)-3-oxopentanoic acid methyl ester (1.0 g), polyphosphoric acid (10 g) and dioxane (10 mL) was heated at 130° C. for 17 hours. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phases washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound, 1.5 g.
Workup
- temperatureThe mixture was cooled to room temperature
- custompartitioned between ethyl acetate and water
- extractionThe aqueous phase was extracted with ethyl acetate
- washthe combined organic phases washed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-57bb94635cdd481fb547286d172bb295
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858640B2
Reaction notes
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