Trimethylsilyl iodide → 5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol

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Reaction Steps

A solution of 2-(6-benzyloxy-5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.52 g; 993 μmol), in acetonitrile (40 ml) is treated with trimethyl silyl iodide (0.353 ml; 2.483 mmol; 2.5 eq.) at 50° C. for 2 hours and then at 20° C. for 16 hours, in a 100 ml three-necked flask. After evaporation, the reaction mixture is taken up in a mixture of dichloromethane (50 ml) and water (50 ml) and is then separated by settling out. The aqueous phase is extracted with dichloromethane (250 ml); the extracts are combined, dried over magnesium sulfate, and evaporated to give a compound which is purified by chromatography on silica gel (10 g, 35 μm silica), elution being carried out with a mixture of cyclohexane and ethyl acetate (60/40 vol/vol). The fractions containing the expected compound are combined and evaporated, resulting in a solid which is triturated in diisopropyl ether so as to obtain 5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol, (0.215 g; 50%), the characteristics of which are as follows:

Provenance & Evidence