Methyl iodide → HCID 57809817, compound

HRID 2105994Notes

Reaction equation

HRID 2105994 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([C:8]([CH3:31])([CH3:30])[CH2:9][C:10]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[C:14]([CH2:23][OH:24])=[CH:13]2)[CH:7]=1.[CH3:34]I>C(#N)C.[Ag-]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([C:8]([CH3:30])([CH3:31])[CH2:9][C:10]([OH:29])([C:25]([F:27])([F:28])[F:26])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[C:14]([CH2:23][O:24][CH3:34])=[CH:13]2)[CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 57809756HCID 57809756, compound

Product 1

HCID 57809817HCID 57809817, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-3-hydroxymethyl-1H-quinolin-4-one (51.5 mg) and silver(I) oxide (127 mg) in acetonitrile (3 mL) was added methyl iodide (68.5 p-L). After heating at 50° C. for 15 hours, the reaction mixture was filtered and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 50%-70% ethyl acetate-hexanes) to give the title compound as a white solid (37.5 mg).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography with silica gel (eluted with 50%-70% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-6431785a2ad2437ca1f60b22463c88e4
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

Loading…