Sodium hydride → HCID 11206895, compound

HRID 856630Notes

Reaction equation

HRID 856630 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1.CC1C=CC(S([O-])=O)=CC=1.[Na+].[H-].[Na+]>C1COCC1.O>[C:9]([CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)#[N:10]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 792052-Bromo-6-methylpyridineHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 11206895HCID 11206895, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-fluorophenylacetonitrile (3.97 g), 2-bromo-6-methylpyridine (5.00 g) and sodium 4-methylphenylsulfinate (10.48 g) in THF (125 ml) was added sodium hydride (2.35 g, 60%) at 0° C. under argon atmosphere, and the mixture was heated to reflux for 3 hours. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:4), to give 2-(α-cyano-4-fluorobenzyl)-6-methylpyridine (5.51 g) as yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained residue was separated
  8. custompurified by column chromatography (ethyl acetate:hexane 1:4)

Sources & evidence

ORD record
ord-0b7ae18e18f44b0face7940f888acf62
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…