1-(Trimethylsilyl)prop-1-yne → HCID 86667270, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-chloropyridine (1.00 g, 5.20 mmol), 1-(trimethylsilyl)-1-propyne (0.846 mL, 5.72 mmol), copper(I) iodide (99 mg, 0.52 mmol), and tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.08 mmol) were taken up in toluene (14 mL) in a microwave vial. Tetra-N-butylammonium fluoride (1M in THF) (6 mL, 6.00 mmol) was added and the reaction vessel was sealed and heated at 100° C. for 20 min in a microwave reactor. After cooling, the mixture was filtered through diatomaceous earth, and then concentrated in vacuo. The product was purified by flash chromatography using a gradient of EtOAc in heptane (0-50%) to give the title compound (530 mg, 67% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 2.11 (s, 3 H), 7.38 (dd, 1 H), 7.51 (s, 1H), 8.37 (d, 1 H); MS (ES+) m/z 152 [M+H]+.

Provenance & Evidence