Trimethylsilyl cyanide → HCID 71236677, compound

HRID 920357Notes

Reaction equation

HRID 920357 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=2)=[C:11]([F:13])[CH:12]=1)(=O)=O.[F-].[CH2:24]([N+:28](CCCC)(CCCC)CCCC)CCC.C[Si](C#N)(C)C>C(#N)C>[F:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[F:21])[O:14][C:10]1[N:9]=[CH:8][C:7]([CH2:6][C:24]#[N:28])=[CH:12][C:11]=1[F:13]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 86676390HCID 86676390, compound

Product 1

HCID 71236677HCID 71236677, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (6-(3,4-difluorophenoxy)-5-fluoropyridin-3-yl)methyl methanesulfonate (8 g, 11.28 mmol) and tetrabutylammonium fluoride (5.90 g, 22.56 mmol) in acetonitrile (100 mL) was added trimethylsilyl cyanide (3.02 mL, 22.56 mmol). The reaction mixture was stirred at 80° C. for 2 hr., and then concentrated under reduced pressure. The crude product was purified bysilica gel chromatography eluting with Hex/EtOAc (5:1) to give get 2-(6-(3,4-difluorophenoxy)-5-fluoropyridin-3-yl)acetonitrile (3 g, 89%).

Workup

  1. concentration, and then concentrated under reduced pressure
  2. customThe crude product was purified bysilica gel chromatography
  3. washeluting with Hex/EtOAc (5:1)
  4. customto give

Sources & evidence

ORD record
ord-8c9b38ce5cad45039b88a6bdfc1e48dd
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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