Triethylamine → Tert-butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)carbamate

Participants

Reaction Steps

The sub-titled compound was prepared from N-(1 adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 2(i)) (0.37 g), tert-butyl (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)prop-2-yn-1-ylcarbamate (Example 11(i)) (0.54 g), copper (I) iodide (0.004 g), bis-triphenyphosphine palladium dichloride (0.014 g), triethylamine (6 ml) and anhydrous acetonitrile (6 ml) by the method of Example 2(iii). The crude product was purified by chromatography on silica gel eluting with, iso-hexane:ethyl acetate (8:1 to 4:1) to afford the sub-titled compound (0.28 g) as a yellow gum.

Provenance & Evidence