Diisopropylamine → (1-[4-(4-oxo-2-phenyl-8-trimethylsilanylethynyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

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Reaction Steps

Copper(I) iodide (1 mg, 0.005 mmol) and bis(benzonitrile)dichloro palladium(II) (2 mg, 0.005 mmol) were dissolved in toluene (1 mL) with stirring. Tri-tert-butylphosphine (2 mg, 0.01 mmol), diisopropylamine (0.017 ml, 0.118 mmol), {1-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50 mg, 0.091 mmol) and (trimethylsilyl)acetylene (0.015 mL, 0.109 mmol) were added, the vial was sealed, and reaction mixture was stirred at RT under an atmosphere of argon for 3 h. The mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, gradient 0 to 10% ethyl acetate in DCM) to afford the title compound as a white solid (51 mg, 100%). LCMS (Method G): RT=5.30 min, [M+H]+=564.

Provenance & Evidence