Hydrogen Peroxide → HCID 58015512, compound

Participants

Reaction Steps

5-(2-methoxyethoxy)-2-(2-(trimethylsilyl)ethynyl)nicotinonitrile (4.23 g, 15 mmol) was dissolved in acetone (60 mL). To the solution was added 3 M sodium carbonate (62 ml, 185 mmol) and hydrogen peroxide (31 ml, 308 mmol) dropwise, and it was stirred at room temperature for 4 h. After completion, the reaction was cooled to 0° C. and to it was slowly added sodium thiosulfate (200 mL) with stirring. The aqueous layer was extracted with DCM (×3, 200 mL), and the combined organics were concentrated and purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield 2-ethynyl-5-(2-methoxyethoxy)nicotinamide (2.0 g, 59% yield).

Provenance & Evidence