Triethylamine → 6-Bromo-5-methylpyridine-2-carbonitrile

HRID 541424Notes

Reaction equation

HRID 541424 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

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 133766782-Bromo-3-methylpyridine 1-oxide2×

Product 1

HCID 219283226-Bromo-5-methylpyridine-2-carbonitrileYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux and stiffed overnight in an oil bath
  3. concentrationconcentrated under reduced pressure
  4. 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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