Butyl Acetate → Ethyl 1-ethyl-5-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-pyridinecarboxylate
Reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12][CH:11]=1.[C:25](OCCCC)(=O)C>>[CH2:6]([N:4]1[CH:3]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[C:17](=[O:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5]1)[CH3:25]Participants
Conditions
- Temperature
- 90 °C
Procedure
N,N-Dimethylformamide dimethylacetal (3.9 ml) was added to a solution of ethyl 4-(4-fluorophenyl)-3-oxobutanoate (1310 mg) in n-butyl acetate (15 ml) at room temperature, and the mixture was stirred at 90° C. for five hours. The solvent was distilled off under reduced pressure, and ethanol (20 ml) was added, followed by addition of ethylamine (2 M solution in THF, 4.4 ml). After stirring at 60° C. for two hours, ethylamine (2 M solution in THF, 3.0 ml) was added and the mixture was further stirred at 60° C. for two hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->70:1 (v/v)] to give 985 mg of the title compound as an oily substance.
Workup
- distillationThe solvent was distilled off under reduced pressure, and ethanol (20 ml)
- additionwas added
- additionfollowed by addition of ethylamine (2 M solution in THF, 4.4 ml)
- stirringAfter stirring at 60° C. for two hours
- additionethylamine (2 M solution in THF, 3.0 ml) was added
- stirringthe mixture was further stirred at 60° C. for two hours
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->70:1 (v/v)]
Sources & evidence
- ORD record
- ord-b9d8c4a4d1f94721affcfb553fb38ac0
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933103B2
Reaction notes
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