Dimethylformamide → 3-Dimethylamino-2-(3-fluoro-pyridine-2-carbonyl)-acrylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]([C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])[CH3:2].[CH3:16][N:17]([CH3:20])[CH:18]=O>OC1CCOC1>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:6]([C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])=[CH:16][N:17]([CH3:20])[CH3:18])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 3-(3-fluoro-pyridin-2-yl)-3-oxo-propionic acid ethyl ester (3) (15 mg, 0.07 mmol) in 3-hydroxytetrahydrofuran (2 mL) was added slowly dimethylformamide diethylacetale (0.085 mL, 0.5 mmol) at room temperature. The mixture was stirred at 50° C. for 6 h. After completion of the reaction, solvent was evaporated under vacuum to get the crude 3-dimethylamino-2-(3-fluoro-pyridine-2-carbonyl)-acrylic acid ethyl ester (4) (18 mg, crude) as a brown sticky liquid LC-MS: 267.4 (M+H). The crude compound was used in the next step without purification.
Workup
- customAfter completion of the reaction, solvent
- customwas evaporated under vacuum
Sources & evidence
- ORD record
- ord-356bdc5af48e41458b71ac005109c3a6
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199987B2
Reaction notes
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