3-Buten-1-ol → 4-Hydroxy-3-[4-(4-hydroxy-but-1-enyl)-phenyl]-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile

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Reaction Conditions

Reaction Steps

To a stirred suspension of 3-(4-iodo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (60 mg, 0.15 mmol), triethylamine (0.1 mL), Pd(OAc)2 (3 mg), P(o-Tol)3 (9 mg), and MgO (18 mg, 0.45 mmol) was added 0.1 mL of but-3-en-1-ol in a single portion. The resulting mixture was heated to 150° C. using microwave reactor for 20 min, then filtered, concentrated and purified by reverse phase HPLC to give the titled compound. MS (ESI) m/e 399 (M+H)+; 1H NMR (500 MHz, DMSO-d6): δ 2.35 (q, J=5 Hz, 2H), 3.53 (t, J=5 Hz, 2H), 6.28 (dt, J=15.91, 7.02 Hz, 1H), 6.45 (d, J=15.91 Hz, 1H), 6.60 (s, 1H), 7.27 (d, J=8.42 Hz, 2H), 7.39 (d, J=8.11 Hz, 2H).

Provenance & Evidence