Triethylamine → 6-Bromo-5-methylpyridine-2-carbonitrile
Reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[CH2:10]([N:12](CC)CC)C.[Si](C#N)(C)(C)C>C(#N)C>[Br:1][C:2]1[N:3]=[C:4]([C:10]#[N:12])[CH:5]=[CH:6][C:7]=1[CH3:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-bromo-3-methylpyridine 1-oxide (compound 350.1, 5.65 g, 30.1 mmol, 1.00 equiv) in acetonitrile (50 mL) were added triethylamine (6.10 g, 60.3 mmol, 2.00 equiv) and TMSCN (8.90 g, 3.00 equiv). The resulting solution was heated to reflux and stiffed overnight in an oil bath, then cooled to ambient temperature and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:5) as eluent to yield 2.00 g (34%) of the title compound as a yellow solid.
Workup
- temperatureThe resulting solution was heated
- temperatureto reflux and stiffed overnight in an oil bath
- concentrationconcentrated under reduced pressure
- customThe residue was purified
Sources & evidence
- ORD record
- ord-41ecc919343f4ac589479dc8fa7bf9af
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871790B2
Reaction notes
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