2-Chloroquinoline → 2-((Trimethylsilyl)ethynyl)quinoline

Participants

Reaction Steps

2-Chloroquinoline (1.02 g, 6.17 mmol), CuI (12.1 mg, 0.622 mmol), and PdCl2(PPh3)2 (22.7 mg, 0.0317 mmol) were dissolved in triethylamine (20.6 mL), followed by stirring for 5 min. To the resulting mixture, trimethylsilyl acetylene (1.34 mL, 9.44 mmol) was added dropwise at 60° C., followed by heating. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:10). When the reaction was completed, the reactant was cooled down to room temperature and extracted with a saturated aqueous solution of NaCl and ethyl acetate, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:10, R.f: 0.4), to thereby obtain 2-((trimethylsilyl)ethynyl)quinoline (1.289 g, 93%) as brown oil.

Provenance & Evidence