Trimethylsilyl cyanide → 2-Fluoro-4-iodopyridine-5-acetonitrile

HRID 1640872Notes

Reaction equation

HRID 1640872 reaction equation
C[Si]([C:5]#[N:6])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:26][C:27]1[C:28]([I:34])=[CH:29][C:30]([F:33])=[N:31][CH:32]=1>C(#N)C.C(Cl)(Cl)Cl.C(O)(C)C>[F:33][C:30]1[N:31]=[CH:32][C:27]([CH2:26][C:5]#[N:6])=[C:28]([I:34])[CH:29]=1

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 66674459HCID 66674459, compound

Product 1

HCID 667382812-Fluoro-4-iodopyridine-5-acetonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Combine trimethylsilyl cyanide (297 mg, 3.0 mmol) and tetrabutylammonium fluoride (785 mg, 3.0 mmol) in 20 mL of acetonitrile under nitrogen. Add 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.63 g, 2.0 mmol) to the above solution. Stir the mixture for 2 h at RT. Dilute the mixture with chloroform/IPA (3/1). Wash the solution with water and subsequently with saturated aqueous sodium chloride. Dry it over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (5% methanol in DCM) to afford the title compound as a yellow, waxy solid (500 mg, 96%). MS (ES) m/z 263 [M+1]+.

Workup

  1. washWash the solution with water
  2. dry with materialDry it over sodium sulfate
  3. concentrationConcentrate the solution in vacuo
  4. customPurify by column chromatography (5% methanol in DCM)

Sources & evidence

ORD record
ord-175be167f4b0419ca036836f8201cb56
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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