Dimethylformamide → 5-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one
Reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.C1(CBr)CC1.CN(C)C=O>O1CCCC1.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:1][CH:2]2[CH2:4][CH2:3]2)[CH:13]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
KOtBu (0.68 g) was added to a solution of 5-bromo-1H-pyridin-2-one (1.00 g) in tetrahydrofuran (20 mL) at room temperature. After stirring for 30 min, cyclopropylmethyl bromide (0.77 mL) and dimethylformamide (3 mL) were added to the suspension and the resulting mixture was warmed to 70° C. After stirring the mixture at 70° C. for 2 h, the reaction was complete. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with water (2×20 mL) and brine (20 mL). Then, the solution was dried (MgSO4) and the solvent was removed to give the title compound as a colorless oil. Yield: 1.18 g (90% of theory). Mass spectrum (ESI+): m/z=228/230 (Br) [M+H]+
Workup
- stirringAfter stirring the mixture at 70° C. for 2 h
- temperatureThe mixture was cooled to room temperature
- washwashed with water (2×20 mL) and brine (20 mL)
- dry with materialThen, the solution was dried (MgSO4)
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-b5a71e7fb9d246489a61219e1d3763d3
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575157B2
Reaction notes
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