Sodium hydride → 4-Chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridine

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Reaction Conditions

Reaction Steps

4-Chloro-1H-pyrrolo[2,3-b]pyridine (170 mg, 1.114 mmol) was dissolved in tetrahydrofuran (2 mL) under nitrogen atmosphere. After cooling to 0° C., 40% NaH (30 mg, 1.224 mmol) was added. The resulting reaction mixture was stirred for 15 minutes and then heated at 80° C. for 3 hours after adding SEM-Cl (185 mg, 1.114 mmol). The heated reaction mixture was cooled to room temperature and then extracted with dichloromethane and water. The organic layer was separated and washed with sodium chloride aqueous solution. The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1) to give the target compound as a yellow oil (235 mg, 0.83 mmol, 74% yield).

Provenance & Evidence