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

HRID 383458Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[CH:5][CH:4]=1.N1C2C(=CC=CC=2)C=C1.[CH3:27][S:28]N1C(=O)C2C(=CC=CC=2)C1=O.[Br-].[Mg+2].[Br-].[OH-].[Na+]>CC(N(C)C)=O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([S:28][CH3:27])=[CH:10]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

customThe phases were separated
customthe organic solvents were evaporated
customThe residue was purified by flash chromatography with heptane/EtAc 20:1

Sources & evidence

ORD record: ord-4e417572ea814b32b66b80e5309f9427
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367665B2

Reaction notes

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