Triethylamine → 2-Cyano-3-fluoropyridine

HRID 887638

Reaction equation

HRID 887638 reaction equation
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si]([C:13]#[N:14])(C)C.C(N(CC)CC)C>CC#N>[F:1][C:2]1[C:3]([C:13]#[N:14])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 70604082-Cyano-3-fluoropyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 3-fluoro-pyridine 1-oxide (0.99 g, 8.75 mmol), trimethylsilyl cyanide (4.80 ml, 35.0 mmol), and triethyl amine (1.84 ml, 13.2 mmol) in 100 ml of CH3CN was heated at reflux overnight. The solvents were removed, under reduced pressure and the residue was partitioned between EtOAc and saturated NaHCO3. The organic portion was separated, dried with Na2SO4, filtered, condensed, the crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes). The titled compound was obtained as a light yellowish solid. MS (ES+): 123.1 (M+H)+. Calc'd for C6H3FN2—122.10.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvents were removed, under reduced pressure
  4. customthe residue was partitioned between EtOAc and saturated NaHCO3
  5. customThe organic portion was separated
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customcondensed
  9. customthe crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes)

Sources & evidence

ORD record
ord-e568494b6bbb429ab93068d83e27aa88
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Linked notes

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