Ethyl bromoacetate → HCID 59596525, compound
Reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[CH2:18]([O:17][C:15]([C:14]1[N:4]([CH3:3])[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[C:11]=1[NH2:12])=[O:16])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
Sodium hydride (9.0 g, 60% dispersion, 225 mmol) was suspended in DMF (150 mL) and cooled to 0-5° C. A solution of 4-methylamino-nicotinonitrile (20.0 g, 150 mmol) in DMF (100 mL) was added dropwise over ca. 20 minutes and the resulting mixture stirred cold for 30 minutes and then treated with a solution of ethyl bromoacetate (34.0 g, 225 mmol) in DMF (50 mL). The solution was allowed to warm to room temperature over 1 hour. The mixture was partitioned between ethyl acetate and water and the aqueous further extracted with ethyl acetate. The combined organic layers were washed with water (×2), brine, dried (MgSO4) and evaporated. Trituration of the resultant residue with ethyl acetate gave the title compound (12.2 g, 37%) as a yellow solid. 1H NMR (CDCl3) 1.44 (3H, t, J=7.1 Hz), 3.88 (3H, s), 4.43 (2H, q, J=7.1 Hz), 5.09 (2H, br s), 7.10 (1H, dd, 1H, J=6.1, 1.0 Hz), 8.35 (1H, d, J=6.1 Hz), 8.88 (1H, d, J=1.0 Hz).
Workup
- temperatureto warm to room temperature over 1 hour
- customThe mixture was partitioned between ethyl acetate and water
- extractionthe aqueous further extracted with ethyl acetate
- washThe combined organic layers were washed with water (×2), brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-3154acbfb9ce4041861fe4327265d765
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855216B2
Reaction notes
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