Cesium carbonate → 6-hydroxy-4-oxo-3-[4-(1H-pyrazol-5-yl)phenyl]-7H-thieno[2,3-b]pyridine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a 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) and MgO (18 mg, 0.45 mmol) in 2 mL DMF and 2 mL dioxane, was added Cs2CO3 (0.45 mL, 1M solution in H2O), followed by 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (38 mg, 0.2 mmol), and Pd(PPh3)4 (10 mg, 0.008 mmol). The reaction was heated to 130° C. using microwave reactor for 15 min, filtered, concentrated and purified by reverse phase HPLC to give the titled compound. MS (ESI) m/e 335 (M+H)+; 1H NMR (500 MHz, DMSO-d6): δ 6.61 (s, 1H), 7.00 (s, 1H), 7.43 (d, J=8.42 Hz, 2H), 7.49 (d, J=8.42 Hz, 2H), 8.04 (s, 1H).

Provenance & Evidence