Diisopropylamine → HCID 67417872, compound

Participants

Reaction Steps

To a solution of 5-bromo-1-methyl-3-{[2-(trimethylsilyl)ethoxy]methoxy}pyridin-2(1H)-one (2.92 g, 8.74 mmol) in 20 mL THF was added trimethylsilylacetylene (1.72 g, 17.47 mmol), copper (I) iodide (166 mg, 0.874 mmol), diisopropylamine (1.25 mL, 8.74 mmol), and PdCl2(dppf)-DCM adduct (713 mg, 0.874 mmol). This mixture was microwaved in a sealed vial at 145° C. for 10 minutes. After cooling, the mixture was filtered to remove solids, evaporated, and purified by flash chromatography (50 g silica gel, 0-40% ethyl acetate in hexane) to afford 1-methyl-3-{[2-(trimethylsilyl)ethoxy]methoxy}-5-[(trimethylsilyl)ethynyl]pyridin-2(1H)-one as a dark, viscous oil (2 g, 65% yield). LCMS [M+H]+=352.6

Provenance & Evidence