1,10-Phenanthroline → 1-(1-(7-methoxyquinolin-4-yloxy)propan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-hydroxypropan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-one (0.052 g, 0.22 mmol) and 4-iodo-7-methoxyquinoline (0.063 g, 0.22 mmol) in 3.0 mL of DMF was added cesium carbonate (Cs2CO3, 0.072 g, 0.22 mmol), 1,10-phenanthroline (0.020 g, 0.11 mmol) followed by copper iodide (CuI) (0.021 g, 0.11 mmol) in a microwave vial. The mixture was heated to 140° C. for 45 minutes. The mixture was then diluted with 40 mL of water and 60 mL of EtOAc. The organic phase was separated, washed with 30 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a MS-triggered Prep-HPLC to give light organic film 1-(1-(7-methoxyquinolin-4-yloxy)propan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-one (0.015 g, 17% yield). MS (ESI pos. ion) m/z (MH+): 393.1. Calc'd Exact Mass for C22H20N2O3S: 392.12.

Provenance & Evidence