Dimethyl Sulfoxide → 4'-Methyl-N-((6-methylpyridin-3-yl)methyl)-5-(oxiran-2-yl)biphenyl-3-carboxamide

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Reaction Conditions

Reaction Steps

A mixture of sodium hydride (60% in mineral oil, 0.85 g, 21.2 mmol) in dimethyl sulfoxide (75 mL) was cooled to −10° C. Trimethylsufoxonium iodide (4.66 g, 21.2 mmol) in DMSO (25 mL) was added dropwise over a 10 mM period. The mixture was warmed to room temperature and stirred for an additional hour. The mixture was cooled to 0° C. and 5-formyl-4′-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide (3.65 g, 10.6 mmol) in DMSO (25 mL) was added dropwise over a 10 minute period. The mixture was warmed to room temperature and stirred for 1 hour. The mixture was poured onto ice and extracted with ethyl acetate (3×150 mL). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The mixture was purified by column chromatography using methylene chloride:methanol gradient (2-10%) to afford the title compound as a yellow oil. LC-MS: 358.8 [M+1]+.

Provenance & Evidence