Water → HCID 57437662, compound

HRID 924578Notes

Reaction equation

HRID 924578 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[C:7]([CH3:9])[N:8]=1.F[C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].O>CN(C)C=O>[CH3:3][C:4]1[N:5]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH:6]=[C:7]([CH3:9])[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 678552-FluorobenzonitrileHCID 178430880HCID 178430880, compound

Product 1

HCID 57437662HCID 57437662, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

Sodium hydride (8.65 grams 60%, 0.216 mol) was stirred in 75 mL of anhydrous dimethylformamide. To this was added dropwise a solution of 2,4-dimethylimidazole (20.75 grams, 0.216 mol) in 100 mL of DMF. After stirring at ambient temperature for 1 hour a solution of 2-fluorobenzonitrile (23.0 mL, 0.216 mol) in 75 mL of DMF was added dropwise. This was stirred at 50° C. for 2 hours and then at ambient temperature for 16 hours. The mixture was then poured into water and the product extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate. The crude product was chromatographed (silica gel) and eluted with 19:1 dichloromethane-methanol then 9:1 dichloromethane-methanol to afford the product as a solid. LCMS data confirmed structure.

Workup

  1. additionwas added dropwise
  2. waitat ambient temperature for 16 hours
  3. extractionthe product extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe crude product was chromatographed (silica gel)
  7. washeluted with 19:1 dichloromethane-methanol

Sources & evidence

ORD record
ord-7b627e9bb18f4ca0948db65c0fc60840
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Reaction notes

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