Morpholine → HCID 68182917, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL microwave vial was charged with 6-chloro-4-(2-naphthyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide (0.140 g, 0.282 mmol, tris(dibenzylideneacetone)dipalladium(0) (0.0129 g, 0.0141 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.0163 g, 0.0282 mmol) and cesium carbonate (0.2758 g, 0.8466 mmol). The vial was flushed with Ar and 1,4-dioxane (4.4 mL) and morpholine (0.0738 mL, 0.847 mmol) were added. The reaction mixture was sealed and heated at microwave irradiation to 140° C. for 1 hour. Solvent was evaporated, and the residue was purified using column chromatography on silica gel (24 g Analogix column, gradient hexane to 50% EA in hexane over 20 minutes) to provide the title compound (0.030 g, 18%). LCMS (FA) ES+: 547. 1H NMR (400 MHz, DMSO) δ 7.94-7.88 (m, 4H), 7.53-7.51 (m, 2H), 7.30-7.27 (m, 1H), 6.50 (s, 1H), 5.69 (s, 1H), 4.87 (d, 1H), 4.53 (d, 1H), 4.11 (d, 1H), 3.87 (d, 1H), 3.64-3.61 (m, 4H), 3.50-3.45 (m, 2H), 3.06-3.03 (m, 4H), 0.79-0.74 (m, 2H), −0.06 (s, 9H).

Provenance & Evidence