I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[F-].[K+].[CH3:38][OH:39]>C1(C)C=CC=CC=1.[Cu](I)I>[CH3:38][O:39][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:3]=1
A mixture of 3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (0.520 g, 1.32 mmol), 1,10-phenanthroline (0.238 g, 1.32 mmol), copper iodide (0.251 g, 1.32 mmol) and potassium fluoride (40% on alumina) (1.05 g, 7.26 mmol) in methanol (2.7 mL) and toluene (13 mL) was purged with argon and heated at reflux for 14 hours. After cooling, the mixture was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (5-25% EtOAc in hexanes) to give 3-methoxy-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (0.260 g, 66% yield) as a brown gum.
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