Water → 1-[5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-one

HRID 896785

Reaktionsgleichung

Reaktionsgleichung von HRID 896785
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:10]([CH:11]=[O:12])=[C:4]2[CH:3]=1.C([Mg]Br)#C.O.O1C[CH2:28][CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:10]([C:11](=[O:12])[C:26]#[C:27][CH3:28])=[C:4]2[CH:3]=1

Komponenten

5

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 219486825-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehydeHCID 178418486HCID 178418486, Verbindung

Produkt 1

HCID 219922331-[5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-oneAusbeute 62 %

Versuchsvorschrift

To a solution of 5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (0.93 g, 3.4 mmol) in tetrahydrofuran (20 mL) at −78° C. was added ethynyl-magnesium bromide (16 mL, 0.5 M in tetrahydrofuran, 8.0 mmol). The mixture was allowed to warm to room temperature and stirred for 1 hour. Water was added to the reaction and the resulting mixture was extracted with ethyl acetate. The ethyl acetate phase was dried (magnesium sulfate), filtered and concentrated to a solid residue. This residue was dissolved in dichloromethane (50 mL) and manganese dioxide (5 g) was added. This slurry was stirred at room temperature for 2 hours. The manganese dioxide was removed by filtration and the filtrate was concentrated to a solid. This solid was purified by flash chromatography (dichloromethane) to give 1-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-one (0.63 g, 62% for two steps) as a white solid. 1H-NMR (CDCl3): δ 8.52 (d, 1H), 8.47 (d, 1H), 7.69 (q. 2H), 7.18 (t, 2H), 7.07 (dd, 1H), 3.00 (s, 1H); 19F-NMR (CDCl3): δ −111.69; MS m/z 299 (M+1).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated to a solid residue
  5. dissolutionThis residue was dissolved in dichloromethane (50 mL)
  6. additionmanganese dioxide (5 g) was added
  7. stirringThis slurry was stirred at room temperature for 2 hours
  8. customThe manganese dioxide was removed by filtration
  9. concentrationthe filtrate was concentrated to a solid
  10. customThis solid was purified by flash chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0dd7f73f29db4e5fa9c59dcb199b21e4
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919352B2

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