Phenylacetylene → HCID 118624439, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[(Z)-{[(6-bromopyridin-2-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (200 mg, 0.514 mmol, 1 eq) in degased THF (2 mL) was added in a microwave tube under argon tetrakis(triphenylphosphine)palladium (0) (59.4 mg, 0.051 mmol, 0.1 eq), copper iodide (14.6 mg, 0.077 mmol, 0.15 eq) N,N-diisopropylethylamine (0.358 ml, 2.06 mmol, 4 eq) and phenylacetylene (157 mg, 1.54 mmol, 3 eq). The mixture was heated in the microwave at 120° C. for 15 min. The mixture was concentrated, diluted with ethyl acetate and filtered over a celite cartridge. The solvent was evaporated and the residue was purified by chromatography on silica gel to afford 2-methyl-3-[(Z)-phenyl({[6-(phenylethynyl)pyridin-2-yl]methoxy}imino)methyl]-1,2,4-oxadiazol-5(2H)-one (115 mg, 52% yield).

Provenance & Evidence