Methyl iodide → HCID 58966895, compound

HRID 1948244Notes

Reaction equation

HRID 1948244 reaction equation
[OH:1][CH2:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:9]2=[O:22])=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:28]>CN(C=O)C.CCOC(C)=O>[CH3:28][O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:13]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[CH:11]=[CH:10][C:9]2=[O:22])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69349835HCID 69349835, compound

Product 1

HCID 58966895HCID 58966895, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to Scheme 24 Step 3: A mixture of 1-(4-(hydroxymethyl)benzyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (1 eq, 0.25 mmol, 0.08 g), NaH (55%, 1.5 eq, 0.37 mmol, 18 mg) and iodomethane (3 eq, 0.75 mmol, 0.11 g) in DMF (2 mL) was stirred at room temperature overnight. The crude was diluted with AcOEt. The organic layer washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 5 g SiO2, CH2Cl2/MeOH 99/1), yielding the title compound (0.14 mmol, 46 mg, 55%) as white solid.

Workup

  1. washThe organic layer washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 5 g SiO2, CH2Cl2/MeOH 99/1)

Sources & evidence

ORD record
ord-8d32d1484a514fdf87ca757d5761f320
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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