Methyl iodide → HCID 58503945, compound

HRID 2407713Notes

Reaction equation

HRID 2407713 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[CH3:16][N:8]1[CH:9]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:11]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178498874HCID 178498874, compound

Product 1

HCID 58503945HCID 58503945, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The compound prepared in Example 130 (0.204 g) was suspended in N,N-dimethyl formamide (4 mL) and cooled to 0° C. Potassium carbonate (0.279 g) was added and then iodomethane (0.069 mL). The reaction mixture was stirred at 0° C. for 30 minutes and then warmed to room temperature and stirred at room temperature for further 1 hour. The reaction mixture was diluted with ethyl acetate and washed sequentially with sodium bicarbonate aqueous solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography to furnish the title compound (0.130 g) having the following physical data.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred at room temperature for further 1 hour
  3. washwashed sequentially with sodium bicarbonate aqueous solution and brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-b11925ec082b4e35b730e210a8ef83af
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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