Water → 3-(Benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-3-yl)pyridin-2-amine dihydrochloride

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Reaction Steps

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 0.125 g, 0.332 mmol), pyridin-3-ylboronic acid (0.0490 g, 0.399 mmol), bis(triphenylphosphine)palladium(II) chloride (0.00700 g, 0.00997 mmol), and sodium carbonate (0.106 g, 0.997 mmol) were combined in DME (10 mL), and water (5 mL) and heated overnight at 80° C. The reaction mixture was cooled and partitioned between dichloromethane and water. The layers were separated, and the organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography to afford the title compound as the free base. The free base was dissolved in dichloromethane and 2M HCl in ether was added. The mixture was concentrated to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-3-yl)pyridin-2-amine dihydrochloride (0.109 g, 87.6% yield). 1H NMR (DMSO-d6) δ 9.27 (m, 1H), 8.81 (d, 1H), 8.75 (d, 1H), 8.48 (d, 1H), 8.08 (m, 1H), 7.97 (m, 1H), 7.66 (d, 2H), 7.43 (m, 2H), 7.37 (m, 1H), 6.82 (s, 1H), 5.45 (s, 2H), 2.31 (s, 3H). Mass spectrum (apci) m/z=375.1 (M+H-2HCl).

Provenance & Evidence