Aniline → 5-morpholino-7-oxo-N-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A 2 mL microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (100 mg, 316 μmol), molybdenumhexacarbonyl (42 mg, 160 μmol), trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium (II) (4.6 mg, 4.9 μmol), tri-tert-butylphosphonium tetrafluoroborate (2.8 mg, 12.0 μmol), tetrahydrofuran (500 μL), aniline (45 μL, 483 μmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (32 μL, 210 μmol). The vial was immediately sealed, magnetically stirred and heated via microwave irradiation to 125° C. for 6 minutes. The mixture was cooled to room temperature, and loaded onto Isolute functionalized silica column (PE-AX/SCX-2). The column was washed with methanol and the product was eluted with 7N methanolic ammonia. The methanolic ammonia fractions were combined and concentrated in vacuo. The resulting solid was purified using preparative high-pressure liquid chromatography to give 5-morpholino-7-oxo-N-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide (51), (3.88 mg, 10.9 μmol) as a yellow solid.

Provenance & Evidence