Trimethylsilylacetylene → 5-Fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine

Participants

Reaction Steps

To a mixture of 2-bromo-5-fluoropyridin-3-amine (3.3 g, 17.3 mmol), TEA (7.3 mL, 51.9 mmol), PdCl2(PPh3)2 (1.2 g, 1.73 mmol), and Cu(I)I (0.33 g, 1.73 mmol) in THF (50 mL) at 0° C. under nitrogen was added a solution of (trimethylsilyl)acetylene (3.39 mL, 34.6 mmol). The mixture was stirred at RT for 2 h and then concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1) to afford 2.0 g (915) of 5-fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine as a yellow solid. MS (ESI): m/z=209.1 [M+1]+.

Provenance & Evidence