Diisopropylethylamine → ethyl 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

Participants

Reaction Steps

To a degassed solution of ethyl 2-ethynyl-4-methylthiazole-5-carboxylate (0.10 g, 0.51 mmol) and (2-azido-1,1-difluoroethyl)benzene (0.14 g, 0.77 mmol) in tetrahydrofuran (5 mL) was added N,N-diisopropylethylamine (0.10 mL, 0.61 mmol), and copper(I) iodide (0.002 g, 0.01 mmol). The reaction mixture was stirred at ambient temperature under nitrogen for 17 hours, and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid (0.13 g, 67%): 1H NMR (300 MHz, CDCl3) δ 8.24 (s, 1H), 7.45-7.31 (m, 5H), 5.02-4.93 (m, 2H), 4.20 (q, J=7.1 Hz, 2H), 2.65 (s, 3H), 1.33 (t, J=7.1 Hz, 3H); MS (ES+) m/z 379.3 (M+1).

Provenance & Evidence