Triethylamine → HCID 68683207, compound

Participants

Reaction Steps

A mixture of 2-bromo-5-nitro pyridine (2.03 g, 10 mmol), 3-butyn-1-ol (1.05 g, 15 mmol), copper(I) iodide (19 mg, 0.1 mmol), dichlorobis(triphenylphosphine)palladium (II) (140 mg, 0.02 mmol), triethylamine (5.06 g, 50 mmol) in acetonitrile (30 mL) was stirred for 4 h. The reaction mixture was evaporated to dryness and loaded onto a Biotage KPSil60A cartridge, and purified by flash chromatography using Et2O-DCM (1:9) as eluent to afford 4-(5-nitropyridin-2-yl)but-3-yn-1-ol as an oil (1.42 g, MS m/e MH+ 193). This oil (1 g, 5.21 mmol) was stirred in methanol (50 mL) and 10% palladium on carbon (0.2 g) was added and the reaction stirred under an atmosphere of hydrogen. The reaction was filtered through Celite® and concentrated in vacuo to afford the title compound as an oil (0.87 g). 1H NMR δ 7.99 (1H, s), 6.93 (2H, s), 3.86 (2H, t), 3.55 (2H, s), 2.73 (2H, t), 1.70-1.74 (2H, m), 1.60-1.62 (2H, m); MS m/e MH+ 167.

Provenance & Evidence