Trimethylsilylacetylene → Furo(3,2-b)pyridine

Participants

Reaction Steps

To a solution of PdCl2(PPh3)2 (1.4 g, 2.0 mmol) and CuI (0.4 g, 2.1 mmol) in TEA (100 mL) and THF (200 mL) under nitrogen was added a mixture of 2-bromo-3-acetoxy-pyridine (13.1 g, 60.6 mmol) and TMS-acetylene (7.0 g, 71 mmol) in THF (100 mL) in one portion. The mixture was stirred at room temperature for 1 hour. Then quenched with saturated NaHCO3 (50 mL) and MeOH (50 mL). The mixture was stirred at 80° C. for 2 hours. After cooling, the mixture was extracted with ether. The organic phase was dried and concentrated. The residue was subject to column chromatography to afford Furo[3,2-b]pyridine (1.54 g, 21%). 1H NMR (CDCl3, 400 MHz) δ 8.55 (m, 1H), 7.84 (m, 1H), 7.75 (m, 1H), 7.72 (m, 1H), 6.99 (m, 1H).

Provenance & Evidence