[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[CH:5]=[N:6][CH:7]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:28]#[N:29])[CH2:27][CH2:26][C:21]3([O:25][CH2:24][CH2:23][O:22]3)[CH2:20][CH2:19]2)=[N:16][CH:17]=1.CN(CC)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I.O>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:3]=1)[C:8]([NH:10][C:12]1[CH:17]=[N:16][C:15]([C:18]2([C:28]#[N:29])[CH2:27][CH2:26][C:21]3([O:22][CH2:23][CH2:24][O:25]3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)=[O:9]A solution of 5-bromopyridine-3-carboxamide (734 mg), 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.18 g) described in Reference Example 82, copper (I) iodide (35 mg), N,N-dimethylethylamine (33 mg) and potassium carbonate (1.01 g) in 1,4-dioxane (5 ml) was stirred at 100° C. for six hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give 5-bromo-N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]nicotinamide (213 mg).
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