Tris(furan-2-yl)phosphane → Tradipitant

Participants

Reaction Conditions

Reaction Steps

Combine 4-[3-(3,5-bistrifluoromethylbenzyl)-5-tributylstannanyl-3H-[1,2,3]triazol-4-yl]-pyridine (489 g, 740 mmol) and toluene (1 L), add (2-bromopyridin-3-yl)-(2-chlorophenyl)-methanone (240 g, 810 mmol) in toluene (500 mL). Next, add tris(dibenzylideneacetone)dipalladium (16.95 g, 18.5 mmol) and toluene (300 mL). Add tri-2-furylphosphine (17.35 g, 74 mmol) in toluene (200 mL) and heat the reaction mixture to reflux (113° C.). Upon completion of the reaction, remove the solvent by rotary evaporation and purify the crude product by flash column chromatography (dichloromethane/ethyl acetate gradient). Treat the material with activated charcoal in ethyl acetate, wash with 5% aqueous trithiocyanuric acid trisodium salt solution, and recrystallize (ethyl acetate/hexane) to give the title compound. MS(IS) 588 (M+1). TLC (3% MeOH/CH2Cl2) Rf=0.17. 1H NMR (400 MHz, CDCl3): 5.46 (s, 2H); 7.19 (m, 5H); 7.36 (dd, 1H, J=4.9, 7.8); 7.45 (s, 2H); 7.59 (m, 1H); 7.83 (s, 1H); 7.93 (dd, 1H, J=1.5, 7.8); 8.56 (dd, 1H, J=1.5, 4.9); 8.70 (d, 2H, J=5.9).

Provenance & Evidence