Water → 1-[Tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

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Reaction Steps

4-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (2.84 g, 9.2 mmol), zinc cyanide (650 mg, 5.5 mmol), and zinc dust (120 mg, 1.8 mmol) were suspended in dimethylacetamide (40 mL). The mixture was degassed thoroughly, bis(tri-t-butylphosphine)palladium (511 mg, 0.46 mmol) was added, and the mixture was stirred at 80° C. for 3d. The mixture was poured into water (80 mL) and filtered. The solids were washed with ethyl acetate and the filtrates were combined. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated. The oily residue was triturated with hexanes, the solution was decanted and the solvent was evaporated to give 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (676 mg, 2.25 mmol, 25% yield).

Provenance & Evidence