Morpholine → HCID 68183034, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 5-allyl-2-bromo-4-(3,4-dichlorophenyl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylate (0.51 g, 1.1 mmol),tris(dibenzylideneacetone)dipalladium(0) (98.3 mg, 0.107 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (124 mg, 0.215 mmol) and cesium carbonate (1.29 g, 3.97 mmol) was evacuated and filled with argon, followed by addition of 1,4-dioxane (12 mL) and morpholine (0.281 mL, 3.22 mmol). The mixture was heated at 100° C. overnight. The mixture was then concentrated in vacuo and the residue was purified by silica gel chromatography. Final purification by HPLC afforded pure product as a white solid (0.136 g, 26%). LCMS (AA) ES+: 482, 484. 1H NMR (400 MHz, DMSO) δ 7.55 (d, J=8.4 Hz, 1H), 7.31 (d, J=2.0 Hz, 1H), 7.22 (s, 1H), 7.07 (dd, J=8.4, 2.0 Hz, 1H), 5.98 (s, 1H), 5.70 (dt, J=17.0, 7.2 Hz, 1H), 5.06 (t, J=13.4 Hz, 2H), 4.41 (s, 1H), 3.66 (t, J=4.7 Hz, 4H), 3.41 (s, 3H), 3.19-3.05 (m, 4H), 2.68 (ddd, J=31.0, 13.9, 7.4 Hz, 2H).

Provenance & Evidence