Methyl iodide → HCID 86686255, compound

HRID 1021318Notes

Reaction equation

HRID 1021318 reaction equation
[C:1](O)(C(F)(F)F)=O.C([O:12][C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:24][N:23]([C:25]3[C:26]([F:33])=[C:27]([CH2:31][OH:32])[CH:28]=[CH:29][CH:30]=3)[CH2:22]2)=[CH:15][CH:14]=1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.ClCCl>[F:33][C:26]1[C:27]([CH2:31][OH:32])=[CH:28][CH:29]=[CH:30][C:25]=1[N:23]1[CH2:22][CH:21]([CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13](=[O:12])[N:18]([CH3:1])[CH:17]=2)[CH2:24]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 68309917HCID 68309917, compound

Product 1

HCID 86686255HCID 86686255, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 ml) was added to a mixture of [3-(3-{[(6-tert-butoxypyridin-3-yl)oxy]methyl}azetidin-1-yl)-2-fluorophenyl]methanol (146 mg) and dichloromethane (1 ml), followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by basic silica gel column chromatography (CHCl3/methanol). The purified product thus obtained was mixed with DMF (2 ml), and potassium carbonate (100 mg) and methyl iodide (68 mg) was added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and CHCl3 and water were added to the residue. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/methanol) to obtain 5-({1-[2-fluoro-3-(hydroxymethyl)phenyl]azetidin-3-yl}methoxy)-1-methylpyridin-2(1H)-one (82 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by basic silica gel column chromatography (CHCl3/methanol)
  3. customThe purified product thus obtained
  4. additionwas added
  5. stirringby stirring at room temperature for 5 hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3 and water
  7. additionwere added to the residue
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (CHCl3/methanol)

Sources & evidence

ORD record
ord-22ac69a21b724e29a666d8ce0e8a6b4d
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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