8-Hydroxyquinoline → 3-(2,5-Dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-1H-pyrazole

Temperatur

110 °C

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole (6.8 g) in N-methyl-2-pyrrolidone (68 ml) were sequentially added cesium carbonate (27.4 g), 8-quinolinol (1.2 g), copper oxide (I) (0.6 g) and 1-fluoro-3-iodobenzene (7.4 ml), and the mixture was stirred at 110° C. for 2 hours. This reaction mixture was cooled to room temperature, and toluene (80 ml) was added thereto, and then the mixture was filtered through Celite. After adding a 1M aqueous solution of sodium hydroxide (80 ml) to the filtrate, the mixture was extracted with toluene. The resulting organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1) to give the titled compound (10.4 g).

1. temperatureThis reaction mixture was cooled to room temperature
2. filtrationthe mixture was filtered through Celite
3. additionAfter adding a 1M aqueous solution of sodium hydroxide (80 ml) to the filtrate
4. extractionthe mixture was extracted with toluene
5. washThe resulting organic layer was sequentially washed with water
6. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1)

ORD-Eintrag

ord-be681fdb8c0f4f5e8dfdcac87443dbe7

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846746B2