Triphenylphosphine → HCID 22282149, compound

Participants

Reaction Steps

6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2.71 g, 13.1 mmol) was dissolved in toluene (45 mL). Vinyl tributyltin (5 g, 15.8 mmol) and triphenylphosphine (103 mg, 3.93 mmol) were added, followed by Pd(PPh3)4 (151 mg, 0.13 mmol). The reaction mixture was heated at reflux for 2 hours, allowed to cool to room temperature, and then treated with saturated aqueous KF solution for 30 minutes. The precipitated solid (tributyltin fluoride) was removed by filtration. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was washed with hexane to give 1,3-dimethyl-6-vinyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2.50 g, 96%) as a pale yellow powder.

Provenance & Evidence