2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 7-methoxy-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

3-Iodo-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine (3.89 g, 13.50 mmol) was flow purged with nitrogen for 30 minutes, then treated with tetrahydrofuran (135 mL). The reaction mixture was cooled to −78° C. Butyllithium (5.40 mL, 13.50 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 30 minutes. 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.75 mL, 13.50 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 2.5 hours. The reaction mixture was poured onto water and extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 100% heptane to 30% ethyl acetate/heptane) to provide the title compound (2.75 g, 70% yield).

Provenance & Evidence