Morpholine → HCID 56971358, compound

Participants

Reaction Conditions

Reaction Steps

To a 2.0-5.0 mL microwave vial was added a solution of 2-bromo-4-(4-chlorophenyl)-6-methyl-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (0.0400 g, 0.112 mmol) and morpholine (0.02934 mL, 0.3364 mmol) in anhydrous 1,4-dioxane (1.500 mL, 19.22 mmol) and degassed under nitrogen for 10 min. Cesium carbonate (0.1700 g, 0.5216 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.0195 g, 0.0336 mmol) were added followed by tris(dibenzylideneacetone)dipalladium(0) (0.0103 g, 0.0112 mmol). The reaction mixture was sealed and heated via microwave to 140° C. and allowed to stir for 40 minutes. The reaction was cooled to ambient temperature and quenched by the addition of a solution of 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 submitted for HPLC purification to afford the product (0.0080 g, 19.0%) as a white solid. LC/MS (AA) ES+ 361, 363, 365. 1H NMR (dmso-d6, 400 MHz): d 7.51 (1H, s), 7.41-7.39 (2H, m), 7.25-7.23 (2H, m), 5.03 (1H, J=4.80, Hz, t), 3.80-3.66 (5H, m), 3.46-3.40 (1H, m), 3.11-3.09 (4H, m), 2.84 (3H, s).

Provenance & Evidence