Réaction #792223

Équation de réaction

DMF

3-(5-fluoro-3-pyridinyl)-1H-pyrazole

methyl 6-bromo-2-pyridinecarboxylate

cesium carbonate

→

Methyl 6-[3-(5-fluoro-3-pyridinyl)-1H-pyrazol-1-yl]-2-pyridinecarboxylate

Solvants

water

Conditions de réaction

Traitement

1. 1
   AutreThe entire reaction mixture
2. 2
   Températurewas then cooled to room temperature
3. 3
   ExtractionThe reaction mixture was then extracted with ethyl acetate
4. 4
   AutreThe organic phase was separated off
5. 5
   Autredried
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by chromatography on silica gel

Mode opératoire

30 ml of DMF were added to 1.88 g (11.5 mmol) of 3-(5-fluoro-3-pyridinyl)-1H-pyrazole (preparation cf. step 2), 2.50 g (11.5 mmol) of methyl 6-bromo-2-pyridinecarboxylate, 92.0 mg (1.15 mmol) of copper (II) oxide, 7.54 g (23.10 mmol) of cesium carbonate and 1.22 g (3.47 mmol) of iron(III) acetylacetonate, and the mixture was stirred at 90° C. for 60 hours. The entire reaction mixture was then cooled to room temperature, and water was added. The reaction mixture was then extracted with ethyl acetate. The organic phase was separated off, dried, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel. This gave 191 mg (5.0% of theory) of methyl 6-[3-(5-fluoro-3-pyridinyl)-1H-pyrazol-1-yl]-2-pyridinecarboxylate.

Source