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 [1.24 g, Reference Example 13(p)] in acetonitrile (100 mL) was treated with iodotrimethylsilane (820 μl). The reaction mixture was stirred at 50° C. for 2 hours and then concentrated in vacuo. The residue was treated with water (40 mL) and the mixture was extracted three times with dichloromethane (100 mL). The combined organic phases were washed with brine (40 mL), then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (1:1, v/v) to give the title compound (686 mg) as a white foam. TLC: RF=0.27 (cyclohexane/ethyl acetate: 1/1). MS: EI (70 eV); m/z=447 M+. (45%); 292 (100%).

Provenance & Evidence