Triethylamine → Ethyl(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)acetate

Participants

Reaction Steps

A solution of ethyl {N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}acetate, (24 mg, 0.06 mmol), 3-methyl-furan-2-carboxylic acid (3-ethynyl-phenyl)-amide (20 mg, 1.5 eq), bis(triphenylphosphine)palladium(II) dichloride (4.1 mg, 0.1 eq), and triphenyl phosphine (0.4 mg, 0.025 eq) in anhydrous DMF (0.5 mL) under a nitrogen atmosphere was added triethylamine (0.05 mL, 5 eq) followed by the addition of copper(I) iodide (2.2 mg, 0.2 eq). The reaction mixture was stirred at RT for 15 minutes and then poured into saturated aq NaHCO3 and extracted with EtOAc (1×). The organic extract was washed with brine (1×) and dried over anhydrous Na2SO4. The organic phase was filtered and concentrated. The residue was purified by chromatography (EtOAc-Hexanes 1:4 to EtOAc). The product containing fractions were combined and concentrated to give the title compound (14 mg, 47%).

Provenance & Evidence