Methyl iodide → 6-Methoxy-3,3-dimethylindolin-2-one

HRID 892201Notes

Reaction equation

HRID 892201 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.[CH3:14]N(CCN(C)C)C.[Li]CCCC.IC>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])[NH:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 222415386-Methoxy-3-methyl-1,3-dihydro-indol-2-oneHCID 178418339Butyllithium

Product 1

HCID 222416036-Methoxy-3,3-dimethylindolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

To a cooled solution (−78° C.) of 6-methoxy-3-methyl-1,3-dihydro-indol-2-one (679 mg, 3.83 mmol, example 77) in THF (13 mL) is added TMEDA (1.16 mL, 7.66 mmol) followed by dropwise addition of 2.5M n-BuLi (3.06 mL, 7.66 mmol). The mixture is stirred 15 min then warmed to −25° C. Iodomethane (275 μL, 4.40 mmol) is added dropwise and stirred for 30 min. Reaction is quenched with sat NH4Cl soln, warmed to room temp 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, 35% ethyl acetate in hexanes) to give the title compound as a white crystalline solid. MS (ESI) 192 (M+H)+.

Workup

  1. stirringstirred for 30 min
  2. customReaction
  3. customis quenched with sat NH4Cl soln
  4. temperaturewarmed to room temp
  5. additiondiluted with EtOAc
  6. dry with materialWashed organic layer with sat NH4Cl soln, brine, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (silica, 35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d257a4a7c4b94205a56784f4e7b3df6e
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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