Diethylamine → 4-Hydroxy-3-[4-(4-hydroxybut-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To an ambient slurry of 3-(4-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.050 g, 0.14 mmol), but-3-yn-1-ol (0.030 g, 0.42 mmol), copper(I) iodide (0.005 g), triphenylphosphine (0.009 g, 0.03 mmol) and diethyl amine (0.15 mL, 1.4 mmol) in DMF (1.5 mL) was added dichlorobis(triphenylphosphine)palladium(II) (0.002 g, 0.003 mmol) in a single portion. The reaction was heated at 120° C. for 20 min in a microwave, cooled to room temperature, filtered, concentrated and purified by RP-HPLC to afford the title compound. MS (ESI) m/e 334.9 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ ppm 12.02 (br s, 1H), 7.39 (d, J=9, 2H), 7.35 (d, J=9, 2H), 6.94 (s, 1H), 3.59 (t, J=9, 2H), 2.57 (t, J=9, 2H).

Provenance & Evidence