tert-butyl N-(prop-2-yn-1-yl)carbamate → Tert-butyl({1-[(6-bromopyridin-2-yl)methyl]-1h-1,2,3-triazol-4-yl}methyl)carbamate

Participants

Reaction Steps

2-(Azidomethyl)-6-bromopyridine (Example 470 Step 1) (700 mg, 3.29 mmol) and tert-butyl prop-2-yn-1-ylcarbamate (510 mg, 3.29 mmol) were combined in t-BuOH (6.0 mL) and water (3.0 mL). CuSO4.5H2O (41 mg, 0.16 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (130 mg, 0.66 mmol) in water (2.0 mL). The reaction was stirred at room temperature for 2 h. The solution was subsequently diluted with saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Purification by flash chromatography (40-100% EtOAc/hexanes) afforded the title compound as a colorless solid.

Provenance & Evidence