Hydrochloric Acid → 3-(Benzyloxy)-N-(4-methylthiazol-2-yl)-5-(1-phenylvinyl)pyridin-2-amine hydrochloride

Participants

Reaction Steps

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.250 g, 0.664 mmol), MeLi (0.519 ml, 0.831 mmol), butyllithium (0.332 ml, 0.831 mmol), and acetophenone (0.0798 g, 0.664 mmol) were reacted according to the method of Example 7. 1M HCl was added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured onto ice and saturated sodium bicarbonate and extracted twice with dichloromethane. The organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (5-10% EtOAc in hexane) to provide the title compound (0.125 g, 47.1% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 7.81 (d, 1H), 7.54 (m, 2H), 7.48 (m, 1H), 7.37 (m, 6H), 7.30 (m, 2H), 6.81 (s, 1H), 5.60 (s, 1H), 5.54 (s, 1H), 5.33 (s, 2H), 2.31 (s, 3H). Mass spectrum (apci) m/z=400.1 (M+H-HCl)

Provenance & Evidence