Potassium Carbonate → 4-chloro-2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-2-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (329 mg, 0.805 mmol) and phenylboronic acid (118 mg, 0.966 mmol) were dissolved in dioxane and then Pd(PPh3)4 (46 mg, 0.04 mmol) was added. After adding 1 M potassium carbonate aqueous solution (1.61 mL), the resulting reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was extracted with dichloromethane and water. The organic layer was washed with sodium chloride aqueous solution, dried with magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1) to give the target compound as a yellow oil (182 mg, 0.51 mmol, 63% yield).

Provenance & Evidence