Triethylamine → 2-Cyano-3-fluoropyridine

HRID 911312Notes

Reaction equation

HRID 911312 reaction equation
[F: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>C(#N)C>[C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 123084Pyridine, 3-fluoro-, 1-oxide

Product 1

HCID 70604082-Cyano-3-fluoropyridineYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 3-fluoropyridine-N-oxide (1.0 g, 8.687 mmol) in anhydrous acetonitrile (100 mL). Add triethylamine (1.319 g, 1.82 mL, 13.031 mmol), trimethylsilylcyanide (3.447 g, 4.63 mL, 34.749 mmol) and heat the mixture to reflux overnight. Cool to ambient temperature and concentrate in vacuo. Dissolve the residue in EtOAc and wash with saturated aqueous NaHCO3. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 17:3) to give the desired intermediate as a solid (746 mg, 70%). GC-MS m/z: 122 (M+).

Workup

  1. temperatureto reflux overnight
  2. concentrationconcentrate in vacuo
  3. dissolutionDissolve the residue in EtOAc
  4. washwash with saturated aqueous NaHCO3
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 17:3)

Sources & evidence

ORD record
ord-3dd873d0c5e14629b3ff0b6ae470974e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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