Morpholine → Methyl 6-allyl-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-allyl-2-bromo-4-(3,4-dichlorophenyl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylate (0.63 g, 1.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (64.7 mg, 0.0706 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (80.7 mg, 0.139 mmol) and cesium carbonate (1.30 g, 3.98 mmol) was evacuated and filled with argon, followed by addition of 1,4-dioxane (37 mL) and morpholine (0.347 mL, 3.98 mmol). The mixture was heated in a sealed microwave tube at 100° C. for 10 h. The mixture was dry loaded on silica gel and purified by chromatography to afford the product as a white solid (0.398 g, 62%). LCMS: (AA) ES+: 481, 483, 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=8.3 Hz, 1H), 7.20 (d, J=2.1 Hz, 1H), 6.92 (dd, J=8.3, 2.1 Hz, 1H), 5.71 (s, 1H), 5.36-5.22 (m, 1H), 5.00-4.90 (m, 2H), 4.78 (dd, J=15.2, 4.9 Hz, 1H), 4.55 (s, 1H), 4.12 (t, J=3.0 Hz, 1H), 3.85-3.77 (m, 4H), 3.73 (d, J=8.0 Hz, 3H), 3.42-3.31 (m, 1H), 3.18 (dd, J=12.0, 7.1 Hz, 4H).

Provenance & Evidence