Cesium carbonate → HCID 68183109, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL vial was added a solution of 2-bromo-4-(4-chlorophenyl)-5,5-dimethyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (0.0434 g, 0.122 mmol) and pyridine-4-boronic acid (0.02802 g, 0.2280 mmol) in 1,4-dioxane (2 mL) and water (0.200 mL). Cesium carbonate (0.1193 g, 0.3661 mmol) was added followed by [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride (0.0120 g, 0.0146 mmol). The reaction mixture was heated to 90° C. and allowed to stir for 18 hr. The reaction was cooled to ambient temperature and quenched by the addition of a saturated aqueous solution of sodium bicarbonate (10 mL) and extracted with EtOAc (10 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified and the enantiomers were separated on a Chiralpak IC 20×250 column using 90/10/01% Hexane/EtOH/DEA, 1.0 mL/minute for 40 minutes. Peak 1 RT=23.9 minutes (0.0050 g, 11%) and Peak 2 RT=39.4 minutes (0.0048 g, 11%) were both isolated as white solids. Absolute configuration of the obtained enantiomers is unknown. LC/MS (AA) ES+ 354, 356, 357, 358. 1H NMR (DMSO-d6, 400 MHz): δ 8.67-8.65 (2H, m), 7.88 (1H, s), 7.80-7.79 (2H, m), 7.43-7.42 (2H, m), 7.16-7.14 (2H, m), 4.48 (1H, s), 1.34 (3H, s), 0.63 (3H, s).

Provenance & Evidence