Water → 3-bromo-5-methylthieno[3,2-c]pyridin-6(5H)-one
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[Br:1][C:2]1[C:6]2=[CH:7][NH:8][C:9](=[O:11])[CH:10]=[C:5]2[S:4][CH:3]=1.[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[Br:1][C:2]1[C:6]2=[CH:7][N:8]([CH3:14])[C:9](=[O:11])[CH:10]=[C:5]2[S:4][CH:3]=1[Br:1][C:2]1[C:6]2=[CH:7][NH:8][C:9](=[O:11])[CH:10]=[C:5]2[S:4][CH:3]=1.[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[Br:1][C:2]1[C:6]2=[CH:7][N:8]([CH3:14])[C:9](=[O:11])[CH:10]=[C:5]2[S:4][CH:3]=1To a suspension of 3-bromothieno[3,2-c]pyridin-6(5H)-one (235 mg, 1.02 mmol) in DMF (3.9 mL) was added sodium hydride (25.7 mg, 1.07 mmol). The mixture stirred 1 h at room temperature, and then methyl iodide (69.9 μL, 1.12 mmol) was added. The reaction stirred a further 1 h at room temperature and then was poured into water (100 mL). The mixture was extracted with dichloromethane (3×50 mL). The combined organic fractions were washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated. Trituration with diethyl ether (˜5 mL) and filtration to collect the resultant solid afforded 120 mg (48%) of the title compound as a tan solid. 1H NMR (400 MHz, CDCl3): δ 7.84 (s, 1 H), 6.91 (s, 1 H), 6.89 (d, J=0.8 Hz, 1 H), 3.75 (s, 3 H); MS (ESI): 244.03, 245.98 [M+H]+; HPLC tR=2.76 min (ZQ3, polar—4 min).
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