(Trifluoromethyl)trimethylsilane → HCID 86730295, compound

Participants

Reaction Steps

To a solution of 2-(5-bromopyridin-2-yl)-2-methylpropanal (1.0 g, 4.4 mmol) and trimethyl(trifluoromethyl)silane (1.1 g, 7.5 mmol) in THF (10 mL) under nitrogen was added the solution of TBAF (230 mg, 0.88 mmol) in THF (5 mL) dropwise at −30° C. The resulting solution was stirred at −30° C. for 1 hour and at ambient temperature for additional 1 hour before the addition of the second batch of TBAF (1.1 g, 4.4 mmol) at ambient temperature. The resulting mixture was stirred at ambient temperature for 20 minutes, then the reaction solution was diluted with water (10 mL), and extracted with EtOAc (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 2-5% EtOAc/hexane) to afford the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.24 (d, J=8.7 Hz, 1H), 4.01 (q, J=7.8 Hz, 1H), 1.51 (s, 6H). MS ESI: [M+H]+ m/z 298, 300.

Provenance & Evidence