Diisopropylamine → N-(1-Adamantylmethyl)-5-bromo-2-methoxyisonicotinamide

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.51 ml of a 2.5M solution in hexanes) was added to diisopropylamine (0.88 ml) in dry tetrahydrofuran,(15 ml) at 65° C. To this solution was added a solution of 5-bromo-2-methoxypyridine (0.82 ml) in dry tetrahydrofuran (10 ml) dropwise over 30 minutes at −65° C. A solution of 1-adamantylmethylisocyanate (1 g) in dry tetrahydrofuran (10 ml) was then added in small portions over 30 minutes at −65° C. The reaction mixture was allowed to warm to 0° C., diluted with saturated brine (20 ml) and extracted into ethyl acetate (3×20 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with dichloromethane:acetone (19:1 to 2.5:1) to afford the sub-titled compound (1.1 g) as a colourless powder.

Provenance & Evidence