Reaction #792223

Reaction equation

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

Solvents

water

Conditions

Workup

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

Procedure

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