Methyl iodide → HCID 59145199, compound

HRID 2389387Notes

Reaction equation

HRID 2389387 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:28])[N:12]([CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:35]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.CCOC(C)=O>[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:28])[N:12]([CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[O:20][CH2:21][C:22]([O:24][CH3:35])=[O:23])[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24961406HCID 24961406, compound

Product 1

HCID 59145199HCID 59145199, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)acetic acid (100 mg) in DMF (2 mL) was added K2CO3 (46 mg) and iodomethane (41 mg) at ambient temperature. The reaction mixture was stirred for 5 hours at the same temperature. The resulting mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-40:60) to give methyl (3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)acetate-.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-40:60)

Sources & evidence

ORD record
ord-0dba46361c6147ab8117b22bbc572f72
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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