Methyl iodide → 6-Methoxy-1,3,3-trimethylindolin-2-one
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customthe cold bath is removed
- stirringstirred for 2 hrs
- customThe reaction is quenched with sat NH4Cl soln
- additiondiluted with EtOAc
Sources & evidence
- ORD record
- ord-8d9fa819fa054953a265f03a5b43cc74
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06635655B1
Reaction notes
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