Morpholine → HCID 68182979, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-allyl-2-bromo-4-(3,4-dichlorophenyl)-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (0.02 g, 0.05 mmol) and morpholine (0.01 mL, 0.14 mmol) in anhydrous 1,4-dioxane (2.00 mL) was degassed under nitrogen for 10 min. Cesium carbonate (72.7 mg, 0.22 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (8.32 mg, 0.01 mmol) was added followed by tris(dibenzylideneacetone)dipalladium(0) (4.4 mg, 0.0048 mmol). The reaction mixture was heated to 140° C. for 1 hour by microwave irradiation. 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 purified by silica gel column chromatography (4 g cartridge, gradient hexanes to 100% EtOAc) to afford the product (22.9 mg, 68%) as a yellow oil. LCMS (AA): ES+ 423, 425, 427. 1H NMR (DMSO-d6, 400 MHz): δ 7.59 (d, J=8.4 Hz, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.16 (dd, J=8.4, 2.0 Hz, 1H), 5.83 (s, 1H), 5.66-5.59 (m, 1H), 5.09-5.05 (m, 2H), 4.30 (t, J=6.0 Hz, 1H), 3.99-3.84 (m, 2H), 3.75-3.68 (m, 5H), 3.70-3.45 (m, 1H), 3.13-3.10 (m, 4H).

Provenance & Evidence