Water → 4-(4-chlorophenyl)-2-(pyridin-4-yl)-4H-cyclopenta[b]thiophen-6(5H)-one

Participants

Reaction Conditions

Reaction Steps

To a 40 mL vial was added a solution of 2-bromo-4-(4-chlorophenyl)-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (0.150 g, 0.458 mmol) and pyridine-4-boronic acid (0.105 g, 0.855 mmol) in a solution of 1,4-dioxane (8.000 mL, 102.5 mmol) and water (0.800 mL, 44.4 mmol). Cesium carbonate (0.448 g, 1.374 mmol) was added followed by [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride (0.045 g, 0.055 mmol). The reaction mixture was heated to 90° C. and allowed to stir for 18 h. The reaction was cooled to ambient temperature and quenched by the addition of a saturated aqueous solution of sodium bicarbonate (10.0 mL) and extracted with EtOAc (10.0 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was dry loaded onto silica gel and then purified using ISCO (12 g cartridge, gradient hexanes to 100% EtOAc over 30 min) to afford the title compound (0.132 g, 84%) as a white solid. LC/MS (AA) ES+ 326, 328. 1H NMR (dmso-d6, 400 MHz): δ 8.65-8.63 (m, 2H), 7.79 (s, 1H). 7.77-7.76 (m, 2H), 7.42-7.40 (m, 2H), 7.30-7.28 (m, 2H), 4.72 (dd, 1H), 3.49 (dd, 1H), 2.81 (dd, 1H).

Provenance & Evidence