[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](I)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([N:25]([CH2:33][C:34]#[CH:35])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:24].C(N(CC)CC)C>[Cu]I.C(#N)C>[C:1]12([CH2:11][NH:12][C:13]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:35]#[C:34][CH2:33][N:25]([CH2:23][CH3:24])[C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH:15]=3)=[O:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2The sub-titled compound was prepared from N-(1 adamantylmethyl)-5-chloro-2-iodoisonicotinamide (Example 2(i)) (0.40 g), tert-butyl ethyl(prop-2-ynyl)carbamate (Example 7(i)) (0.34 g), copper (I) iodide (0.004 g), bis-triphenyphosphine palladium dichloride (0.014 g), triethylamine (5 ml) and anhydrous acetonitrile (5 ml) by the method of Example 2(iii). The crude product was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate (9:1 to 7:3) to afford the sub-titled compound (0.30 g).
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