Water → N-[3-(hydroxyl-pyridin-2-yl-methyl)-pyridin-2-yl]-2,2-dimethyl-propionamide

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Reaction Conditions

Reaction Steps

TMEDA (2.54 ml, 16.8 mmol) is added to a solution of pivaloylamino pyridine (1 g, 5.6 mmol) in diethyl ether (40 ml), and the resulting solution is cooled to −70° C. A solution of 2.5M N-Butyl lithium in hexanes (6.73 ml, 16.8 mmol) is added dropwise to the solution, which turns a golden yellow colour. The solution is allowed to warm to −20° C. and stirred at this temperature for 2 hours. The solution is cooled to −70° C. and a solution of pyridine-3-carbaldehyde (1.16 ml, 12.3 mmol) in THF (20 ml) is added and resulting suspension is allowed to warm to room temperature and stirred overnight. H2O is added and the phases are separated, the aqueous phase is washed with DCM, and the organic phases combined, and concentrated in vacuo to afford a yellow oil. Purification by flash chromatography (SiO2, 70-100% EtOAc in iso-hexane), and drying in vacuo at 45° C. overnight yields N-[3-(hydroxyl-pyridin-2-yl-methyl)-pyridin-2-yl]-2,2-dimethyl-propionamide [M+H]+ 286.

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