Iodine → 2-cyclobutyl-1-(4-methylsulfanyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanol

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To a solution of (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanone (0.6 g, 1.47 mmol) in anhydrous tetrahydrofuran (5 mL) at 0° C. was added a solution of freshly prepared Grignard reagent [To a suspension of magnesium turnings (0.14 g, 5.88 mmol) in anhydrous tetrahydrofuran (5 mL) was added (bromomethyl)cyclobutane (0.44 g, 2.94 mmol) at room temperature. After initiation by iodine, the resulting solution was refluxed for 30 min, and then cooled to room temperature] dropwise. After stirring for 3 h at 0° C., the mixture was poured into brine (10 mL), extracted with ethyl acetate (3×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 25% ethyl acetate/hexanes) afforded 2-cyclobutyl-1-(4-methylsulfanyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanol (90 mg, 18%) as a white solid: LC/MS m/e calcd for C20H22N2OS [M+H]+ 339.48, observed 339.0.

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