Dimethylformamide → 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide
Reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([N:8]([CH3:10])[CH3:9])=[O:7])#[N:4].[Br:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][N:13]=1.[CH3:19][N:20]([CH3:23])C=O>>[Br:18][C:16]1[CH:15]=[CH:14][N:13]=[C:12]([CH:5]([C:3]#[N:4])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7])[CH:17]=1.[Br:11][C:12]1[CH:19]=[N:20][CH:23]=[CH:16][C:17]=1[CH:5]([C:3]#[N:4])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]Participants
Conditions
- Temperature
- 60 °C
Procedure
Sodium hydride (186.2 mg, 4.65 mmol, 60% dispersion in oil) was added to a solution of 2-cyano-N,N-dimethyl-acetamide (373.7 mg, 3.33 mmol) in dimethylformamide (10 mL) at 0° C. The mixture was removed from the ice bath for 20 min, and a solution of 2,4-dibromopyridine (300 mg, 1.33 mmol) in dimethylformamide (3 mL) was quickly added. The mixture was heated at 60° C. for 16 h. The reaction was cooled to room temperature, quenched by addition of 200 μL saturated ammonium chloride and concentrated to a residue. The compound was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide and 2-(3-bromo-pyridin-4-yl)-2-cyano-N,N-dimethyl-acetamide.
Workup
- customThe mixture was removed from the ice bath for 20 min
- temperatureThe reaction was cooled to room temperature
- customquenched by addition of 200 μL saturated ammonium chloride
- concentrationconcentrated to a residue
- customThe compound was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-dbd686e09898417da4dfc09ec43f2c80
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242280B2
Reaction notes
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