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

HRID 2117209Notes

Reaction equation

HRID 2117209 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>[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

5

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 1

HCID 8028TetrahydrofuranSolvent

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) in THF (10.5 mL) is added 60% NaH (132 mg, 3.30 mmol) and the mixture stirred for 15 min. Add dropwise to the reaction mixture iodomethane (215 μL, 3.45 mmol), the cold bath is removed and stirred for 2 hrs. The reaction is quenched with sat NH4Cl soln, warmed to room temp and diluted with EtOAc.

Workup

  1. customthe cold bath is removed
  2. stirringstirred for 2 hrs
  3. customThe reaction is quenched with sat NH4Cl soln
  4. additiondiluted with EtOAc

Sources & evidence

ORD record
ord-ab09af2788b14292b92ce8450c697e66
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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