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

HRID 61002Notes

Reaction equation

HRID 61002 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 the solution of 5-bromo-2-methylpyridine 1-oxide (8.935 g, 47.52 mmol) in acetonitrile (240 mL) was added trimethylsilyl cyanide (TMSCN) (25 mL, 190 mmol) and triethylamine (20 mL, 142.56 mmol). The reaction was heated at 100° C. for 16 h. The mixture was cooled to rt and concentrated in vacuo. The crude was purified by silica gel chromatography using 0-50% EtOAc in hexane to obtain the title compound.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-035056e9ff4d4d83af49545bd64726c4
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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