Triethylamine → 3-Bromopyridine-2-carbonitrile

HRID 423181Notes

Reaction equation

HRID 423181 reaction equation
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([N:11](CC)CC)C.C[Si](C#N)(C)C.[OH-].[Na+]>C(#N)C>[Br:1][C:2]1[C:3]([C:9]#[N:11])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 142763Pyridine, 3-bromo-, 1-oxide

Product 1

HCID 8176943-Bromopyridine-2-carbonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-pyridine 1-oxide (9.4 g, 54 mmol) is dissolved in acetonitrile (60 mL) and triethylamine (15 mL) is added followed by trimethylsilyl cyanide (21.7 mL, 163 mmol). The mixture is heated to 100° C. and stirred for 16 h. The mixture is cooled to 0° C., poured into 250 mL of 5 M aqueous NaOH, and extracted with dichloromethane. The combined extracts are washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified using flash chromatography (Biotage® Si65M, 20% AcOEt/hexane) yields 7.8 g (79%) of the title compound as a yellow solid. GCMS m/e 182 [M−H]−.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionextracted with dichloromethane
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material is purified

Sources & evidence

ORD record
ord-4abb570429de403ea86cc5008a223912
Source dataset
uspto-grants-2012_01
Patent number
US08101761B2

Reaction notes

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