1,4-Dioxane → 1-(6-Fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethanamine

Participants

Reaction Steps

A mixture of tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.4146 g, 0.933 mmol) was dissolved in hydrochloric acid, 4 M solution in 1,4-dioxane (4.66 mL, 18.65 mmol) and the mixture was stirred at rt. After 3.5 h, the mixture was partitioned between DCM (50 mL) and water (50 mL). The acidic aq mixture was washed with DCM (30 mL×2) to remove organic impurities and then basified to ˜pH 10 with 10 N NaOH (3.5 mL), extracted with DCM (50 mL×3). The combined organic layers were washed with water (100 mL×1), brine (100 mL×1), dried over MgSO4, filtered, and concentrated in vacuo to give 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethanamine as an orange syrup: LC-MS (ESI) m/z 345.1 [M+H]+. The orange syrup was carried on crude without further purification.

Provenance & Evidence