Triethylamine → 3-Chloro-6-((trimethylsilyl)ethynyl)isoquinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-3-chloroisoquinoline (240 mg, 1 mmol), ethynyltrimethylsilane (150 mg, 1.5 mmol), triethylamine (150 mg, 1.5 mmol), copper iodide (20 mg, 0.1 mmol), triphenylphosphine (26 mg, 0.1 mmol), and palladium acetate (22.4 mg, 1 mmol) in dry DMF (1 mL) was heated at 65° C. for 30 minutes. The reaction was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic solution was washed with water (20 mL), brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to afford the title compound as a white powder (180 mg, 70%).

Provenance & Evidence