Trimethylsilyl iodide → HCID 22477326, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(6-benzyloxy-5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.5 g; 2.79 mmol) in acetonitrile (120 ml) is placed in a 250 ml three-necked flask at 20° C., and then trimethylsilyl iodide (0.956 ml; 6.97 mmol) is added dropwise. The reaction mixture is heated at 50° C. for 4 hours and is then evaporated to dryness under reduced pressure. The evaporation residue is taken up in dichloromethane (200 ml) and then washed with distilled water (1×200 ml). The extracts are combined, washed with distilled water, dried over magnesium sulfate and evaporated under reduced pressure, to produce the crude compound which is purified by chromatography on a silica cartridge (AIT FlashSmart Pack, BP-0610300-093, 50 g silica), elution being carried out at 15 ml/min with a dichloromethane/ethyl acetate (95/5 v/v) mixture. The fractions containing the expected product are combined and evaporated to give 5-methoxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol (0.87 g; 70%) in the form of an ochre foam, which is used as it is for the following step.

Provenance & Evidence