Triethylamine → 3-[4-(4-Azidobut-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

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To a solution of 4-hydroxy-3-[4-(4-hydroxy-but-1-ynyl)-phenyl]-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (0.23 g, 0.7 mmol) in 5 mL DMF was added triethylamine (0.28 mL, 2 mmol), followed by MsCl (85 μL, 1 mmol). The mixture was stirred at rt for 2 hr, after which NaN3 (0.36 g, 5.6 mmol) was added, and heated to 90° C. overnight. Solvent was removed in vacuo and purified via reverse phase HPLC to afford the titled compound. MS (ESI) m/e 360 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ 2.76 (t, J=6.61 Hz, 2H), 3.52 (t, J=6.44 Hz, 2H), 6.67 (s, 1H), 7.29 (d, J=8.48 Hz, 2H), 7.44 (d, J=8.48 Hz, 2H).

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