Methyl iodide → HCID 23085088, compound

HRID 1727096Notes

Reaction equation

HRID 1727096 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][N:19]([CH3:30])[C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].I[CH3:34]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]([CH2:18][N:19]([CH3:30])[C:20]3[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=3)([O:17][CH3:34])[CH2:15][CH2:16]2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10223112HCID 10223112, compound

Product 1

HCID 23085088HCID 23085088, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-40 °C

Procedure

To the compound (6.0 g) obtained in Example 12 in DMF (50 mL) was added 60% sodium hydride (0.65 g) under cooling with ice-water, followed by stirring at the same temperature for one hour. The reaction mixture was cooled to −40° C., and iodomethane (2.09 g) was added dropwise thereto over twenty minutes. After stirring at −40° C. for one hour and further stirring at −20 to −15° C. for four hours, the reaction mixture was left at −12° C. overnight. The reaction mixture was cooled to −20° C., was mixed with an ice water (100 mL) and was warmed to room temperature. After extracting with ethyl acetate, the organic layer was sequentially washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography [Chromatorex NH™] (eluent; hexane:ethyl acetate=3:1 to 1:1) to yield the titled compound (0.643 g) as a white solid.

Workup

  1. waitover twenty minutes
  2. stirringAfter stirring at −40° C. for one hour
  3. stirringfurther stirring at −20 to −15° C. for four hours
  4. waitthe reaction mixture was left at −12° C. overnight
  5. temperatureThe reaction mixture was cooled to −20° C.
  6. temperaturewas warmed to room temperature
  7. extractionAfter extracting with ethyl acetate
  8. washthe organic layer was sequentially washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe residue was purified by silica gel column chromatography [Chromatorex NH™] (eluent; hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-18155705f68f4f9f9fbeed2c28184d46
Source dataset
uspto-grants-2009_02
Patent number
US07494987B2

Reaction notes

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