Morpholine → HCID 68183333, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-bromo-4-(3,4-dichlorophenyl)-7-oxo-6,7-dihydrothieno[2,3-c]pyridine-5-carboxylate (0.081 g, 0.19 mmol), morpholine (0.0489 g, 0.561 mmol), tris(dibenzylideneacetone)dipalladium(0) (17.1 mg, 0.0187 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (21.6 mg, 0.0374 mmol) and cesium carbonate (183 mg, 0.561 mmol) in 1,4-dioxane (3.0 mL, 38 mmol) was heated to 140° C. for 20 min, and then to 150° C. for another 90 min by microwave irradiation. The mixture was concentrated and purified by chromatography and then preparative HPLC to afford the product as a white solid (5.3 mg, 6.4%). LCMS (FA) ES+: 439.4, 441.4. 1H NMR (400 MHz, DMSO) δ 11.30 (s, 1H), 7.67 (d, J=8.3 Hz, 1H), 7.54 (d, J=1.9 Hz, 1H), 7.25 (dd, J=8.2, 2.0 Hz, 1H), 5.76 (s, 1H), 4.09 (d, J=5.1 Hz, 2H), 3.76-3.63 (m, 4H), 3.59 (s, 3H), 3.23-3.06 (m, 4H).

Provenance & Evidence