Pyridine → (S)-{1-[3-(6-Methyl-pyridin-3-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (10 g, 33.3 mol), 5-hydroxy-2-methylpyridine (4 g, 36.7 mol), copper iodide (6.3 g, 33.3 mol), potassium carbonate (9.2 g, 66.7 mol) and pyridine (33 mL) in sealed tube was heated at 145° C. for six days. The reaction was cooled down to room temperature and filtered, the filtrate was washed with H2O and extracted with CH2Cl2 three times, and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 30:20:1/Hexane:EtOAc:triethylamine to give the title product (3.8 g, 33% yield) as sticky yellow oil.

Provenance & Evidence