Triethylamine → Ethyl N-[6-fluoro-3-[2-(trimethylsilyl)ethynyl]-2-pyridinyl]carbamate

Participants

Reaction Steps

A mixture of compound 57 (4 g, 12.9 mmol), 3.3 ml (23.4 mmol) TMSA (ethynyl-trimethyl-silane), 246 mg (1.29 mmol) Cu(I)iodide, 454 mg (0.65 mmol) PdCl2(PPh3)2 (454 mg, 0.64 mmol) and triethylamine (6.3 ml) was stirred and degassed (N2). The resulting reaction mixture was stirred for 10 hours at 100° C. (closed vessel), cooled and poured into ethyl acetate and H2O. The organic layer was washed with H2O, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (diethyl ether/PE (1/3)) to afford (6-fluoro-3-trimethylsilanylethynyl-pyridin-2yl)-carbamic acid ethyl ester (58) (oil, 1.5 g, 42%). 1H-NMR (200 MHz, CDCl3) δ 7.76 (bt, J=8 Hz, 1H), 7.68-7.60 (bs, 1H), 6.56 (dd, J=8 Hz, 3 Hz, 1H), 4.29 (q, J=8 Hz, 2H), 1.34 (t, J=8 Hz, 3H), 0.3 (s, 9H). (TLC diethyl ether/PE 1/1 Rf 0.39).

Provenance & Evidence