Triethylamine → (S)-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

Participants

Reaction Conditions

Reaction Steps

To the solution of (S)-5-bromo-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]nicotinamide (1.9 g, 3.82 mmol) in anhydrous DMF (19 mL) under nitrogen atmosphere was added sequentially 3-methyl-furan-2-carboxylic acid (3-ethynyl-phenyl)-amide (1.72 g), triethylamine (2.13 mL), bis(triphenylphosphine)palladium(II) dichloride (268 mg), and triphenylphosphine (25 mg). The reaction system was placed under a N2—H2 (1:1) atmosphere and CuI (145 mg) was added in one portion. After the reaction mixture was stirred and heated at 60° C. for 1.5 hours, it was poured into saturated aqueous NaHCO3. The aqueous was extracted with EtOAc (1×), which was subsequently washed with aqueous NaHCO3 (1×), brine (1×), and dried (anhydrous Na2SO4). The organic layer was decanted, evaporated and wrapped with silica gel. Two times column chromatography (EtOAc-Hex:from 1:4 to 1:2; and MeOH—CH2Cl2: 1:100) gave the title compound as yellow foam (2.2 g, 90%).

Provenance & Evidence