Methyl iodide → 6-Methoxy-3-methyl-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (−78° C.) of 6-methoxy-1,3-dihydro-indol-2-one (840 mg, 5.2 mmol, See Quallich, Synthesis 1993, 51–53) in THF (20 mL) is added dropwise TMEDA (1.57 mL, 10.4 mL) followed by dropwise addition of 2.5M n-BuLi (4.16 mL, 10.4 mmol). The mixture is allowed to stir for 15 min then warmed to −25° C. Iodomethane (405 μL, 6.5 mmol) is added dropwise and stirred for 20 min. The 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, 45% ethyl acetate in hexanes) to give the title compound. MS (ESI) 178 (M+H)+.

Provenance & Evidence