Diisopropylamine → 5-morpholino-3-(phenylethynyl)-7H-thieno[3,2-b]pyran-7-one

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (50 mg, 158.1 μmol), phenylacetylene (32.0 mg, 316.2 μmol), trans-dichlorobis(triphenylphosphine)palladium (II) (5.6 mg, 7.9 μmol), copper (I) iodide (1.6 mg, 7.9 μmol) and diisopropylamine (1.0 mL). The mixture was magnetically stirred and heated via microwave irradiation to 100° C. for 20 minutes. The mixture was cooled to room temperature, and then concentrated in vacuo resulting in a brown solid. The solid was dissolved in methanol (1.0 mL) and loaded onto Isolute functionalized silica column (PE-AX/SCX-2). The column was washed with methanol and 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-3-(phenylethynyl)-7H-thieno[3,2-b]pyran-7-one (31) (24.0 mg, 71.1 μmol) as an orange solid.

Provenance & Evidence