Trimethylsilylacetylene → 2-Chloro-6-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]pyridine

Participants

Reaction Steps

2-Azido-6-chloropyridine (500 mg, 3.24 mmol) and trimethylsilylacetylene (545 μL, 3.88 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL) CuSO4.5H2O (40 mg, 0.16 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (128 mg, 0.65 mmol) in water (1.0 mL). The reaction was stirred at room temperature overnight, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated to a crude residue that was purified by flash chromatography (0-40% EtOAc/hexanes) to afford the title compound as a colorless solid.

Provenance & Evidence