Triethylamine → 2-Bromo-4-(prop-1-ynyl)pyridine

Participants

Reaction Steps

To a solution of 2-bromo-4-iodopyridine (2 g, 7.04 mmo, copper(I) iodide (0.080 mL, 2.11 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.407 g, 0.35 mmol) in toluene (85 mL) was added 1-(trimethylsilyl)-1-propyne (1.054 mL, 7.04 mmol), triethylamine (3.24 mL, 23.25 mmol) and tetrabutylammonium fluoride (1 M in THF, 7.04 mL, 7.04 mmol) and the resulting mixture was stirred under an argon atmosphere at r.t. overnight. The mixture was concentrated and the resulting residue was partitioned between water (10 mL) and DCM (10 mL) and poured into a phase separator. The organic phase was collected, and the aqueous phase was extracted once with DCM (10 mL). The combined organics were concentrated and purified by flash chromatography using 0% to 30% EtOAc in heptane to give the title compound (1.195 g, 87% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 2.11 (s, 3 H), 7.42 (dd, 1 H), 7.65 (s, 1 H), 8.35 (dd, 1 H); MS (ES+) m/z 196 [M+H]+; MS (APCI+) m/z 196 [M+H]+.

Provenance & Evidence