1-(Trimethylsilyl)prop-1-yne → 3-Bromo-4-methyl-5-(prop-1-YN-1-YL)pyridine

Participants

Reaction Conditions

Reaction Steps

3,5-Dibromo-4-methylpyridine (0.50 g, 2.0 mmol), 1-(trimethylsilyl)-1-propyne (0.35 mL, 2.4 mmol), copper(I) iodide (0.11 g, 0.60 mmol), tetrakis(triphenylphosphine)palladium(0) (0.023 g, 0.02 mmol) were mixed in toluene (2 mL). The mixture was degassed by a stream of argon for a couple of min. Tetra-n-butylammonium fluoride (1 M in THF) (2.4 mL, 2.4 mmol) was added, and the reaction was heated under N2 at 70° C. overnight. The mixture was partitioned between water containing sat aq. NaHCO3 and EtOAc. The organic phase was dried (MgSO4) and evaporated to give a crude product which was purified by flash chromatography (40 g SiO2, heptane/EtOAc gradient) affording the title compound (0.067 g, 16% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 2.15 (s, 3 H), 2.46 (s, 3 H), 8.48 (s, 1 H), 8.61 (s, 1 H); MS (ES+) m/z 210 [M+H]+.

Provenance & Evidence