Ethylene Glycol → N-(1-Adamantylmethyl)-5-chloro-2-(2-hydroxyethoxy)isonicotinamide

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60%, 0.080 g) was added to ethylene glycol (3 ml) and the resulting suspension stirred under an atmosphere of nitrogen for 30 minutes. To this mixture was added a solution of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 1(ii)) (0.192 g) in anhydrous N-methyl-2-pyrrolidinone (1 ml). The stirring bar was removed and the resulting solution heated in a MARS microwave for 15 minutes (300 Watts, 150° C.). The mixture was cooled and poured into water (50 ml) and extracted into is ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (2×10 ml), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:isohexane (1:1) to afford the sub-titled compound (0.092 g) as a white solid.

Provenance & Evidence