Cesium carbonate → HCID 56971356, compound

Participants

Reaction Conditions

Reaction Steps

2-bromo-4-(4-chlorophenyl)-6-methyl-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (0.0400 g, 0.112 mmol) and pyridine-4-boronic acid (0.02575 g, 0.2095 mmol) were dissolved in a mixture of 1,4-dioxane (2 mL) and water (0.2 mL). Cesium carbonate (0.1096 g, 0.3364 mmol) was added followed by [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride (0.0111 g, 0.0134 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 (10.00 mL) and extracted with EtOAc (10.00 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified using preparative HPLC to afford the product (0.0080 g, 19.0%) as a white solid. LC/MS (AA) ES+ 355, 357, 358, 359. 1H NMR (DMSO, 400 MHz): δ 8.59-8.58 (2H, m), 7.69-7.67 (2H, m), 7.51 (1H, s), 7.44-7.42 (2H, m), 7.31-7.29 (2H, m), 5.00 (1H, J=6.40, Hz, t), 3.95-3.91 (1H, m), 3.71-3.66 (1H, m), 2.50 (3H, s).

Provenance & Evidence