Sodium hydride → HCID 11183726, compound

HRID 856586Notes

Reaction equation

HRID 856586 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1.C1(C)C=CC(S([O-])=O)=CC=1.[Na+].[H-].[Na+]>C1COCC1>[C:7]([CH:6]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1)[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)#[N:8]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 2723791Sodium p-toluenesulfinateHCID 27340872-Bromo-4-methylpyridine

Product 1

HCID 11183726HCID 11183726, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

p-Fluorobenzyl cyanide (4.1 g), 2-bromo-4-methylpyridine (5.2 g) and sodium p-toluene sulfinate (5.4 g) were suspended in THF (50 ml), and to the solution was added a suspension of 40% sodium hydride (1.2 g) in THF (5 ml) under ice-cooling. The mixture was refluxed for 3 hours, the solvent was distilled off, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give 2-(α-cyano-4-fluorobenzyl)-4-methylpyridine (3.1 g) as brown oil.

Workup

  1. additionto the solution was added
  2. temperaturecooling
  3. temperatureThe mixture was refluxed for 3 hours
  4. distillationthe solvent was distilled off
  5. additionwater was added to the mixture
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-67c0473bbdc748acb625468714c65511
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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