Dimethylformamide → 1-(2-(Quinolin-4-yloxy)ethyl)-5-(thiophen-2-yl)pyridin-2(1H)-one
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]1=[O:15].CN(C=O)C.[H-].[Na+].Cl[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[CH:26][CH:25]=1>>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]([O:1][CH2:2][CH2:3][N:4]2[CH:9]=[C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[CH:7]=[CH:6][C:5]2=[O:15])=[CH:25][CH:26]=1Participants
Procedure
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).
Workup
- stirringto stir under inert atmosphere overnight
Sources & evidence
- ORD record
- ord-15225b1b54a04ff0bf8f46e997b8f489
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314087B2
Reaction notes
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