Water → HCID 86639683, compound

Participants

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), 9-benzyl-9-bora-bicyclo[3.3.1]nonane (1.99 mL, 0.997 mmol), PdCl2(dppf) dichloromethane adduct (0.0273 g, 0.0332 mmol), were placed in DMF (6 mL), and water (0.6 mL) and heated to 60° C. for 18 hours. The reaction mixture was cooled and partitioned between water and DCM. The layers were separated and the organic layer was dried, filtered, and concentrated. Crude material was purified by silica gel to give the free base of the title compound (92%). The free base was purified by reverse phase chromatography. The purified free base was dissolved in DCM and 2M HCl was added. The mixture was concentrated to give 5-benzyl-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.038 g, 29.5% yield). 1H NMR (DMSO-d6) δ 7.88 (s, 1H), 7.57 (m, 3H), 7.38 (m, 3H), 7.27 (m, 4H), 7.21 (m, 1H), 6.83 (s, 1H), 5.29 (s, 2H), 3.94 (s, 2H), 2.31 (s, 3H). Mass spectrum (apci) m/z=388.1 (M+H-HCl).

Provenance & Evidence