Methyl iodide → HCID 68527197, compound

HRID 884087Notes

Reaction equation

HRID 884087 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([OH:14])=[CH:9][C:8]=1[F:15])[CH3:2].C(=O)(O)[O-].[Na+].[CH3:22]I.C(=O)([O-])[O-].[K+].[K+].Cl[C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][N:32]=1>CN(C=O)C.O>[CH3:22][CH:5]([NH:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([O:14][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][N:32]=2)=[CH:9][C:8]=1[F:15])[C:4]([O:3][CH2:1][CH3:2])=[O:16]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 516892Sodium BicarbonateHCID 131729741HCID 131729741, compound

Product 1

HCID 68527197HCID 68527197, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl(2,5-difluoro-4-hydroxyphenyl)aminoacetate (1.1 g, 4.8 mmol) in DMF (25 mL) were added sodium bicarbonate (0.44 g, 5.2 mmol) and methyl iodide (1.69 mL, 28.6 mmol), and the resulting reaction solution was stirred for 2 days at room temperature. Water was added to the reaction mixture, and extracted with ethyl acetate. Once the ethyl acetate layer had been washed with water, the ethyl acetate layer was dried with anhydrous magnesium sulfate, and evaporated. The residue was dissolved in DMF (30 mL), and to this resulting solution were added potassium carbonate (0.72 g, 5.2 mmol) and 2-chloro-5-nitropyridine (0.79 g, 5.0 mmol). The reaction solution was stirred for 2.5 days at room temperature. Water was added to the reaction mixture, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was then evaporated, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=8:1), to thereby yield 1.41 g of the title compound.

Workup

  1. customthe resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washOnce the ethyl acetate layer had been washed with water
  4. dry with materialthe ethyl acetate layer was dried with anhydrous magnesium sulfate
  5. customevaporated
  6. dissolutionThe residue was dissolved in DMF (30 mL)
  7. stirringThe reaction solution was stirred for 2.5 days at room temperature
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was then evaporated
  12. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-e966c4036e9848e18cffb6b7b58116cc
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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