Methyl iodide → HCID 67515742, compound

HRID 1502135Notes

Reaction equation

HRID 1502135 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:9]([CH:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[C:6]([N+:23]([O-:25])=[O:24])[N:5]=1.[CH3:26]I>CN(C=O)C>[CH3:26][C:10]([C:9]1[C:4]([CH3:3])=[N:5][C:6]([N+:23]([O-:25])=[O:24])=[CH:7][CH:8]=1)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86693020HCID 86693020, compound

Product 1

HCID 67515742HCID 67515742, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of NaH (60% in oil, 0.8 g, 19 mmol) in DMF (50 mL) was added tert-butyl ethyl (2-methyl-6-nitropyridin-3-yl)propanedioate (4 g, 13 mmol) at room temperature. The mixture was stirred for 1 hour and CH3I (3.7 g, 26 mmol) was added. The mixture was heated to 40° C. for 2 hours. Cooled to ambient temperature, the mixture was poured to ice/water, extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatograph silica gel to give title compound.

Workup

  1. temperatureCooled to ambient temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatograph silica gel

Sources & evidence

ORD record
ord-b2d2a642778248c8aeffa2a79a6124e8
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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