1,3-Bis(diphenylphosphino)propane → HCID 11499796, compound

Participants

Reaction Steps

2-Chloro-4-iodopyridine (340.4 mg, 1.42 mmol) was dissolved in anhydrous toluene (15 mL), after which 4-fluoro-3-methoxyaniline (241.4 mg, 1.7 mmol), tris(dibenzylidineacetone)dipalladium(0) (26.5 mg, 0.028 mmol), 1,3-bis(diphenylphosphino)propane (23 mg, 0.06 mmol), and sodium-tert-butoxide (191.9 mg, 2.0 mmol) were added to the solution. This reaction mixture was stirred at reflux for 12-18 hours, after which the reaction was diluted in dichloromethane and filtered through Celite™. The Celite™ was washed with dichloromethane, and the resulting solution was concentrated to afford the product. This solid was collected and dried for 12-18 hours under vacuum. Purification (Biotage Horizon HPFC chromatography system, SiO2, 90:9:1 dichloromethane:methanol:ammonium hydroxide) yielded a light brown solid (18, 169 mg, 47%); HPLC: Inertsil ODS-3V C18, 30:70[KH2PO4 (0.01M, pH 3.2): CH3CN], 264 nm, Rt 5.2 min, 93.6% purity.

Provenance & Evidence