Indole → 1-(4-methoxyphenyl)-3-(methylthio)-1H-indole

Participants

Reaction Conditions

Reaction Steps

1-(4-methoxyphenyl)-1H-indole (synthesised from indole by an arylation process analogous to that described in step (a) of Example 1 [arylation process also described in J. Org. Chem. 2008, 73 (14), 5529-5535], 1.0 g, 4.48 mmol), 2-(methylthio)isoindoline-1,3-dione (0.95 g, 4.93 mmol) and magnesium bromide (8 mg, 0.045 mmol) were mixed in degassed DMA and stirred under an atmosphere of nitrogen at 90° C. for 90 min. 1M NaOH and EtOAc were added. The phases were separated and the organic solvents were evaporated. The residue was purified by flash chromatography with heptane/EtAc 20:1 to provide 1-(4-methoxyphenyl)-3-(methylthio)-1H-indole in 80% yield. ES/MS m/z: 270.11 (M+H).

Provenance & Evidence