Reaktion #74676

Reaktionsgleichung

Cesium fluoride

5-fluoro-2-iodo-4-(trifluoromethyl)phenol

4-(tributylstannyl)pyridazine

N,N-dimethylformamide

N,N-dimethylformamide

→

product

Ausbeute 62.5%

5-Fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenol

Ausbeute 62.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was capped with a septum
2. 2
   Sonstigethen evacuated
3. 3
   workup.ADDITIONback-filled with argon (5 cycles)
4. 4
   Temperaturthe reaction mixture was cooled to ambient temperature
5. 5
   workup.ADDITIONdiluted with ethyl acetate and water
6. 6
   Filtrationfiltered through diatomaceous earth
7. 7
   WaschenThe solids were washed with additional ethyl acetate
8. 8
   SonstigeThe layers were separated
9. 9
   Waschenthe organic layer was washed successively with water, aqueous lithium chloride, and brine
10. 10
    TrocknenThe organic layer was then dried over sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vacuo
13. 13
    Einengenconcentrated onto diatomaceous earth
14. 14
    Sonstigepurified by automated flash chromatography (24 g SiO2, methylene chloride to 9:1 methylene chloride-methanol)

Vorschrift

Cesium fluoride (570 mg, 3.8 mmol), tetrakis(triphenylphosphine)palladium(0) (220 mg, 0.19 mmol), and copper(I) iodide (72 mg, 0.38 mmol) were added to a solution of 5-fluoro-2-iodo-4-(trifluoromethyl)phenol (Preparation 885, 579 mg, 1.89 mmol) and 4-(tributylstannyl)pyridazine (770 mg, 2.1 mmol) in N,N-dimethylformamide (4 mL, 50 mmol). The sides of the flask were washed down with N,N-dimethylformamide (3 mL, 40 mmol). The flask was capped with a septum then evacuated and back-filled with argon (5 cycles). The reaction mixture was heated at 45° C. After 90 min, the reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and water, and filtered through diatomaceous earth. The solids were washed with additional ethyl acetate. The layers were separated, and the organic layer was washed successively with water, aqueous lithium chloride, and brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in methylene chloride, concentrated onto diatomaceous earth, and purified by automated flash chromatography (24 g SiO2, methylene chloride to 9:1 methylene chloride-methanol) to afford the product as a tan solid (305 mg, 62%).

Quelle