Sodium Cyanide → 4-Iodo-2-cyanopyridine

HRID 1672760Notes

Reaction equation

HRID 1672760 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.[C-:9]#[N:10].[Na+]>CS(C)=O.C(OCC)(=O)C>[C:9]([C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1)#[N:10]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 234368464-Iodo-2-cyanopyridineYield 5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Fluoro-4-iodopyridine (4.99 g, 22.4 mmol) prepared according to a known method (WO2005/041663) was dissolved in dimethyl sulfoxide (75 mL), and the mixture was stirred at 100° C. after adding sodium cyanide (1.21 g, 24.7 mmol). The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by silica gel column chromatography to give 2-cyano-4-iodopyridine (258 mg, 5%).

Workup

  1. washthe organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe residue obtained upon concentration under reduced pressure
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec35c8d5b09346b3bca58c4fa64ae55a
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…