Propargyl alcohol → 3-(3-Pyridyl)-2-propyn-1-ol

Participants

Reaction Steps

A solution of 3-bromopyridine (2.0 g, 12.6 mmol), propargyl alcohol (1.1 mL, 19 mmol), diisopropylethylamine (3.2 mL, 23 mmol), copper iodide (133 mg, 0.7 mmol) and tri-(t-butyl)phosphine (286 mg, 1.4 mmol) in degassed THF (10 mL) was treated with Pd(CH3CN)2Cl2 (181 mg, 0.7 mmol) at 25° C. under N2. After 18 h, the reaction mixture was filtered through celite, washed with ethyl acetate (2×100 mL), and concentrated in vacuo. Purification by flash chromatography (EtOAc) afforded the title compound (1.33 g, 80%) as a yellow oil. MS 134 (M+H)+.

Provenance & Evidence