Dimethylcarbamoyl Chloride → 6-(3-Fluorophenyl)-5-methylpyridine-2-carbonitrile

HRID 2095879Notes

Reaction equation

HRID 2095879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N+:9]=2[O-])[CH:5]=[CH:6][CH:7]=1.[CH3:16][N:17](C)C(Cl)=O.C[Si](C)(C)C#N.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:16]#[N:17])[CH:11]=[CH:12][C:13]=2[CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 66968986HCID 66968986, compound

Product 1

HCID 581585646-(3-Fluorophenyl)-5-methylpyridine-2-carbonitrileYield 99.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution (40 mL) of 2-(3-fluorophenyl)-3-methylpyridine 1-oxide (4.26 g, 21.0 mmol), dimethylcarbamic acid chloride (2.94 g, 27.3 mmol) and trimethylsilanecarbonitrile (2.71 g, 27.3 mmol) in tetrahydrofuran was heated under reflux, and the mixture was stirred for 2 hr. After cooling to room temperature, the reaction solution was divided into two layers with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution and subjected to extraction (3 times) with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography to give the title compound (4.42 g, 99%).

Workup

  1. temperatureunder reflux
  2. extractionsubjected to extraction (3 times) with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cbde3a2661fa44629f5afb2ca92c0d4a
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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