Methyl iodide → 6-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-7-(methoxymethyl)-2H-quinolizin-2-one

HRID 1360708Notes

Reaction equation

HRID 1360708 reaction equation
[H-].[Na+].I[CH3:4].[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[C:13]1[N:14]2[C:19]([CH:20]=[CH:21][C:22]=1[CH2:23][OH:24])=[C:18]([C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1[F:32])[C:17](=[O:33])[CH:16]=[CH:15]2>C1COCC1>[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[C:13]1[N:14]2[C:19]([CH:20]=[CH:21][C:22]=1[CH2:23][O:24][CH3:4])=[C:18]([C:25]1[C:26]([F:32])=[CH:27][CH:28]=[CH:29][C:30]=1[F:31])[C:17](=[O:33])[CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 16065181HCID 16065181, compound

Product 1

HCID 160653126-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-7-(methoxymethyl)-2H-quinolizin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oil free sodium hydride suspended in THF was added iodomethane (0.06 mL) and 6-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-7-(hydroxymethyl)-2H-quinolizin-2-one (Example 50, 40 mg) at 0° C. The mixture was warmed to room temperature and stirred for a couple of hours until reaction complete. The mixture was quenched with water, extracted with ethyl acetate, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel (100% acetone) to give the title compound (22 mg).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel (100% acetone)

Sources & evidence

ORD record
ord-e69dd940723e4bf2b684f1f2c44d273d
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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