Methyl iodide → HCID 18618656, compound

HRID 1919244Notes

Reaction equation

HRID 1919244 reaction equation
[C:1]1([S:7]([NH:10][C:11]2C=CC(I)=CC=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][I:25]>CN(C=O)C>[CH3:11][NH:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[C:1]1[CH:6]=[CH:5][C:24]([I:25])=[CH:3][CH:2]=1)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1377347HCID 1377347, compound

Product 1

HCID 18618656HCID 18618656, compoundYield 196.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To compound 28 (from Example 18) (500 mg, 1.39 mmol) in DMF (10 mL) were added at room temperature K2CO3 (962 mg, 6.96 mmol), followed by methyl iodide (395 mg, 2.78 mmol). The resulting reaction mixture was stirred at room temperature for 16 hours. The solvent is then removed and water was added. The resulting mixture was extracted with ethyl acetate, and the combined organic phases were dried and concentrated. Purification by flash chromatography using hexane:ethyl acetate (8:2) afforded 510 mg (98%) of the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent is then removed
  3. additionwater was added
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. customthe combined organic phases were dried
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c618f662dbbb4b3daba72fb92202f9f0
Source dataset
uspto-grants-2012_05
Patent number
USRE043343E1

Reaction notes

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