Hydrochloric Acid → 1-[1-(4-Fluoro-phenyl)-2-methyl-3,3-dioxo-1,2,3,4-tetrahydro-3lambda*6*-thia-2,4,5-triazaphenanthren-9-yl]-ethanone

Participants

Reaction Conditions

Reaction Steps

DMF (2.6 ml) and water (0.6 ml) in a microwave tube were degassed with N2. 9-Bromo-1-(4-fluoro-phenyl)-2-methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide 399 (100 mg, 0.27 mmol), Pd(OAc)2 (10.6 mg, 0.047 mmol), 1,3-bis(diphenylphosphino)propane (39 mg, 0.09 mmol) and K2CO3 (39 mg, 0.28 mmol) and n-butyl vinylether (154 μl, 1.1 mmol). The mixture was heated in a microwave at 100° C. (200 W, <250 PSi) for 40 min. After cooling, the mixture was diluted with THF (5 ml), acidified with conc. HCl (1 ml) and the mixture was stirred at room temperature for 14 h. The organic phase was diluted with DCM (30 ml), and washed with HCl solution at pH=5-6 (20 ml). The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/EtOAc (95:5) to give the title compound (17 mg, 15%).

Provenance & Evidence