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

HRID 2117208Notes

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

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) 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 for 15 min then warmed to −25° C. Add dropwise iodomethane (275 μL, 4.40 mmol) and let stir for 30 min. The reaction is quenched with sat NH4Cl soln, warmed to room temp and diluted with EtOAc. The organic layer is washed with sat NH4Cl soin, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes) to give 601 mg of title compound as a white crystalline solid. MS (ESI) 192 (M+H)+.

Workup

stirringlet stir for 30 min
customThe reaction is quenched with sat NH4Cl soln
temperaturewarmed to room temp
additiondiluted with EtOAc
washThe organic layer is washed with sat NH4Cl soin
dry with materialbrine, dried over MgSO4
concentrationconcentrated
customThe residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-46635ad7a1004bbaa7c188592d17f5ae
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE040558E1

Reaction notes

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