Triphenylphosphine → Tert-butyl[(5-chloro-3-{[3-(propylsulfonyl)phenyl]ethynyl}pyridin-2-yl)oxy]acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate (Intermediate 182; 160 mg; 0.50 mmol), 1-ethynyl-3-(propane-1-sulfonyl)-benzene (Intermediate 42; 155 mg; 0.74 mmol), bis(triphenylphosphine)palladium (II) chloride (10 mg; 0.01 mmol) and triphenylphosphine (26 mg; 0.10 mmol) is treated with cuprous iodide (3 mg; 0.01 mmol) and TEA (1.10 ml) and heated at 90° C. in a sealed vessel for 15 hours. The mixture was diluted with EtOAc and washed with a saturated NH4Cl solution and brine. The organic phase was dried over MgSO4, concentrated to dryness under reduced pressure affording a sticky solid, which was purified by column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc, affording the title compound as a yellow sticky solid

Provenance & Evidence