Triethylamine → HCID 131735155, compound

Participants

Reaction Steps

To a solution of 1-(6-bromopyridin-2-yl)ethanone (1000 mg, 5.0 mmol) and triethylamine (2.1 mL, 15.0 mmol) at 0° C. in dichloromethane (14 mL) was added trifluoromethyl tert-butyldimethylsilanesulfonate (1.4 mL, 6.2 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated. The residue was purified via flash chromatography (0-30% ethyl acetate in heptanes) to afford 2-bromo-6-(1-((tert-butyldimethylsilyl)oxy)vinyl)pyridine as a colorless oil (1450 mg, 92%). 1H NMR (400 MHz, DMSO-d6) δ 0.22 (s, 6H), 0.98 (s, 9H), 4.62-4.63 (m, 1H), 5.52 (s, 1H), 7.56-7.62 (m, 2H), 7.82 (s, 1H).

Provenance & Evidence