4-Aminomethyltetrahydropyran → 3-Bromo-4-methoxy-N-[(oxan-4-yl)methyl]aniline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Palladium (II) acetate (0.032 g, 0.14 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.179 g, 0.29 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 2-bromo-4-iodo-1-methoxybenzene (0.6 g, 1.92 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.221 g, 1.92 mmol) and sodium-t- butoxide (0.276 g, 2.88 mmol) were suspended in toluene (3.5 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. The mixture was filtered and purified by flash silica chromatography, elution 30% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 3-bromo-4-methoxy-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (0.060 g, 10.42 %) as a brown solid. 60mg of product formed by LC-MS and major product is unknown but doesn't contain pyran signals in NMR and not SM iodide.

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