Triphenylphosphine Oxide → HCID 136200884, Verbindung

Temperatur

80 °C

2-Iodo-4-(6-(trifluoromethyl)pyridin-3-yl)phenol (Preparation 60, 840 mg, 2.30 mmol) was dissolved in acetonitrile (20 mL) and 4-(tributylstannyl)pyridazine (1.10 g, 2.99 mmol), caesium fluoride (698 mg, 4.60 mmol), copper iodide (87 mg, 0.46 mmol) and tetrakis(triphenylphosphine)palladium (0) (266 mg, 0.23 mmol) were added. The reaction mixture was stirred at 80° C. for 18 hours and then partitioned between ethyl acetate and water containing 0.88 ammonia. The resulting mixture was stirred for 15 minutes and then filtered through a pad of celite. The aqueous phase was separated and extracted with ethyl acetate (2×20 mL) and the combined organic phases were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage (10% to 100% EtOAc in heptane over 25 CV) to give a mixture of the title compound and triphenylphosphine oxide. The residue was triturated with dichloromethane to give the title compound (360 mg, 50%) as a white solid.

1. custompartitioned between ethyl acetate and water containing 0.88 ammonia
2. stirringThe resulting mixture was stirred for 15 minutes
3. filtrationfiltered through a pad of celite
4. customThe aqueous phase was separated
5. extractionextracted with ethyl acetate (2×20 mL)
6. washthe combined organic phases were washed with brine
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified on silica gel by Biotage (10% to 100% EtOAc in heptane over 25 CV)
11. customto give

ORD-Eintrag

ord-2db79a1e469a4cc298b616b0ee2928f1

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08772293B2