Methyl iodide → 6-Methoxy-1,3,3-trimethylindolin-2-one

HRID 892202Notes

Reaction equation

HRID 892202 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:18]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[N:9]2[CH3:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222416036-Methoxy-3,3-dimethylindolin-2-one

Product 1

HCID 219318586-Methoxy-1,3,3-trimethylindolin-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution (−5°−0° C.) of 6-methoxy-3,3-dimethyl-1,3-dihydro-indol-2-one (600 mg, 3.14 mmol, example 78) in THF (10.5 mL) is added 60% NaH (132 mg, 3.30 mmol) and is stirred for 15 min. Iodomethane (215 μL, 3.45 mmol) is added to the reaction mixture and stirred for 2 hrs. Quenched reaction with sat NH4Cl soln and diluted with EtOAc. Washed organic layer with sat NH4Cl soln, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes) to give the title compound as a white crystalline solid. MS (ESI) 206 (M+H)+.

Workup

  1. stirringstirred for 2 hrs
  2. customQuenched
  3. customreaction with sat NH4Cl soln
  4. dry with materialWashed organic layer with sat NH4Cl soln, brine, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9cb1dfb2d96f49acb1bb59a35cba22ac
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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