Methyl iodide → HCID 5306292, compound

HRID 734722Notes

Reaction equation

HRID 734722 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])=C2C(O)=O)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:22].C[CH2:24][O:25][C:26]([CH3:28])=[O:27]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:22])[C:10]([CH3:15])=[C:28]2[C:26]([O:25][CH3:24])=[O:27])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 534357904-(4-Chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid

Product 1

HCID 5306292HCID 5306292, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 4, Step 2 (1.0 g, 3.6 mmol, 1.0 equiv) was dissolved in DMF (36 mL) and cooled to 0° C. Sodium Hydride (144 mg, 60% in mineral oil, 3.6 mmol, 1.0 equiv) was added, followed by iodomethane (222 μL, 3.6 mmol, 1.0 equiv). The reaction was allowed to warm to room temperature and stirred for 2 hours. Additional portions of NaH (72 mg, 1.8 mmol, 0.50 equiv) and iodomethane (111 μL, 1.8 mmol, 0.50 equiv) were added and the reaction was stirred for one hour. The reaction mixture was diluted with water and EtOAc. The phases were separated and the organic phase was washed twice with satd. NaCl, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (linear gradient 10→50% EtOAc/Hexanes) to afford 470 mg of the title compound (45%) as an off-white powder. MS (ES+) m/e 294 [M+H]+.

Workup

  1. temperatureto warm to room temperature
  2. stirringthe reaction was stirred for one hour
  3. customThe phases were separated
  4. washthe organic phase was washed twice with satd
  5. dry with materialNaCl, dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (linear gradient 10→50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-1b56cad4286d4ff1bc0b0cc54b95ddfe
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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