Triethylamine → 3-Bromo-6-methylpyridine-2-carbonitrile

HRID 340205Notes

Reaction equation

HRID 340205 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[N+:6]([O-])[CH:7]=1.C[Si]([C:14]#[N:15])(C)C.C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[C:7]([C:14]#[N:15])=[N:6][C:5]([CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 8171645-Bromo-2-methylpyridin-1-ium-1-olate

Product 1

HCID 219527473-Bromo-6-methylpyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-2-methylpyridine 1-oxide (from step 1) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-50% ethyl acetate in hexane to give 3-bromo-6-methylpicolinonitrile.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated en vacuo
  3. customthe residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-6477f9285112491ea6713b42e0232879
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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