Dimethylformamide → HCID 68828054, compound

HRID 734713Notes

Reaction equation

HRID 734713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[C:4]([F:19])[CH:3]=1.[H-].[Na+].COS([O:27][CH3:28])(=O)=O.[CH3:29]N(C=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:29])[C:10]([CH3:15])=[C:9]2[C:16]([O:27][CH3:28])=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Product 1

HCID 68828054HCID 68828054, compoundYield 73%

Procedure

The product of Example 3 Step 2 (3.0 g, 10.08 mmol, 1.0 equiv) was dissolved in 100 mL DMF and NaH (806 mg, 20.15 mmol, 2.0 equiv) was added slowly to the reaction mixture. Me2SO4 (1.9 mL, 20.15 mmol, 2.0 equiv) was added and the reaction was stirred at room temperature for 45 min. The reaction was quenched with water and filtered. The precipitate was washed with water and air dried to provide 2.29 g (73%) of the title compound as a light yellow solid. MS (ES+) m/e 312 [M+H]+

Workup

  1. customThe reaction was quenched with water
  2. filtrationfiltered
  3. washThe precipitate was washed with water and air
  4. customdried

Sources & evidence

ORD record
ord-ae974346bc6d4314bbd9c22ce01d6380
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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