Methyl iodide → HCID 68310279, compound

HRID 1021308Notes

Reaction equation

HRID 1021308 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[CH2:13][CH:12]([O:14][C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][CH:20]=2)[CH2:11]1.CI.[C:24](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[CH2:11][CH:12]([O:14][C:15]2[CH:16]=[CH:17][C:18](=[O:21])[N:19]([CH3:24])[CH:20]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86686247HCID 86686247, compound

Product 1

HCID 68310279HCID 68310279, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-({1-[2-Fluoro-3-(hydroxymethyl)phenyl]azetidin-3-yl}oxy)pyridin-2(1H)-one (160 mg) was mixed with DMF (3 ml), and methyl iodide (114 mg) and potassium carbonate (200 mg) were added thereto, followed by stirring at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were added CHCl3 and water. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 5-({1-[2-fluoro-3-(hydroxymethyl)phenyl]azetidin-3-yl}oxy)-1-methylpyridin-2(1H)-one (106 mg).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionto the residue were added CHCl3 and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-7b633453f48246d99f592f761335c28f
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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