Dimethylformamide → 1-(2-(Quinolin-4-yloxy)ethyl)-5-(thiophen-2-yl)pyridin-2(1H)-one

Participants

Reaction Steps

To a mixture of 1-(2-hydroxyethyl)-5-(thiophen-2-yl)pyridin-2(1H)-one (0.050 g, 0.3 mmol) in DMF (1 mL, 13 mmol) was added sodium hydride (0.080 g, 3 mmol). The resulting mixture was allowed to stir 1.5 hours at ambient temperature. Then 4-chloroquinoline (0.080 g, 0.5 mmol) was added into the mixture and allowed to stir under inert atmosphere overnight. The progress of the reaction was monitored by LC/MS, which showed mostly desired product. The mixture was diluted with CH2Cl2 and water, then extracted the organic layer with CH2Cl2 (3×20 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in-vacuo. The crude material was purified by Reverse-Phase HPLC. This gave the desired product as an off-white solid (0.050 g, 45% yield). MS (ESI pos. ion) m/z (MH+): 349. Calc'd exact mass for C20H16N2O2S: 348. 1H NMR (300 MHz, CDCl3): 8.67 (d, J=4.82, 1H), 8.05 (d, J=8.33 Hz, 1H), 7.95 (d, J=8.33 Hz, 1H), 7.73 (s, 1H), 7.56 (d, J=9.79 Hz, 2H), 7.35 (s, 1H), 7.19 (s, 1H), 6.99 (d, J=2.34, 2H), 6.67 (d, J=4.97 Hz, 1H), 6.58 (d, J=9.35 Hz, 1H), 4.48 (s, 4H), 1.74 (s, 1H).

Provenance & Evidence