O1CCOCC1.Br[C:8]1[CH:9]=[C:10]([CH3:15])[C:11]([NH2:14])=[N:12][CH:13]=1.[I-:16].[Na+].CC(C)(N)C(C)(C)N>[Cu](I)I.O>[I:16][C:8]1[CH:9]=[C:10]([CH3:15])[C:11]([NH2:14])=[N:12][CH:13]=1To dioxane (10 mL) was added 5-bromo-3-methylpyridin-2-amine (2 g, 10.6 mmol), sodium iodide (3.2 g, 21.4 mmoL), copper iodide (0.190 g, 1.06 mmol) and the solution degassed followed by addition of tetramethylethane-1,2-diamine (0.803 mL, 1.06 mmol) this mixture heated at 110° C. overnight. After cooling water was added and extracted the crude product with ethyl acetate. The residue was purified by column chromatography to give 5-iodo-3-methylpyridin-2-amine as a beige solid (2.3 g, 93%).
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