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Sodium hydride → (E)-3-[4-(4-Fluorophenyl)-6-isopropyl-1H-pyrrolo[2,3-b]-pyridin-5-yl]prop-2-enal

HRID 892873
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 892873
C1(NC=CP(=O)(OCC)[O:11][CH2:12][CH3:13])CCCCC1.[H-].[Na+].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:32]([CH:33]=O)=[C:31]([CH:35]([CH3:37])[CH3:36])[N:30]=[C:29]3[NH:38][CH:39]=[CH:40][C:28]=23)=[CH:23][CH:22]=1.O.O.C(O)(=O)C(O)=O>O1CCCC1.O>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[C:32](/[CH:33]=[CH:13]/[CH:12]=[O:11])=[C:31]([CH:35]([CH3:37])[CH3:36])[N:30]=[C:29]3[NH:38][CH:39]=[CH:40][C:28]=23)=[CH:25][CH:26]=1
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Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 89268Diethyl [2-(cyclohexylamino)vinyl]phosphonateHCID 149943844-(4-Fluorophenyl)-6-isopropyl-1H-pyrrolo[2,3-B]pyridine-5-carbaldehyde

Produkt 1

HCID 14994385(E)-3-[4-(4-Fluorophenyl)-6-isopropyl-1H-pyrrolo[2,3-b]-pyridin-5-yl]prop-2-enal

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 11 g (42 mmol) of diethyl 2-(cyclohexylamino)-vinyl-phosphonate in 60 ml of tetrahydrofuran are added dropwise under argon in the course of 10 min to a suspension of 2.52 g (84 mmol) of 80% strength sodium hydride in 60 ml of anhydrous tetrahydrofuran. 9.9 g (35 mmol) of the compound from Example VIII dissolved in 100 ml of tetrahydrofuran are added dropwise at reflux. The mixture is allowed to boil under reflux for 90 min and is cooled, treated with water and extracted several times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and concentrated in vacuo. The residue is dissolved in 300 ml of toluene and heated under reflux for 1 h with 22.9 g (182 mmol) of oxalic acid dihydrate in 350 ml of water. The mixture is cooled, the phases are separated and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness in vacuo. The residue is dissolved in dichloromethane and filtered through 400 g of silica gel 230-400 mesh in a glass suction filter. The mixture is eluted without sucking dry using petroleum ether/ethyl acetate 1:1, the eluate is concentrated in vacuo and the residue is stirred thoroughly in ether.

Aufarbeitung

  1. additionare added dropwise
  2. temperatureat reflux
  3. temperatureunder reflux for 90 min
  4. temperatureis cooled
  5. extractionextracted several times with ethyl acetate
  6. washThe combined organic phases are washed with saturated sodium chloride solution
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue is dissolved in 300 ml of toluene
  9. temperatureheated
  10. temperatureThe mixture is cooled
  11. customthe phases are separated
  12. extractionthe aqueous phase is extracted twice with ethyl acetate
  13. washThe combined organic phases are washed with saturated sodium chloride solution
  14. dry with materialdried over sodium sulphate
  15. concentrationconcentrated to dryness in vacuo
  16. dissolutionThe residue is dissolved in dichloromethane
  17. filtrationfiltered through 400 g of silica gel 230-400 mesh in a glass suction
  18. filtrationfilter
  19. washThe mixture is eluted
  20. customwithout sucking dry
  21. concentrationthe eluate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0078ca3307d4d12a4502c5ea72f5481
Quelldatensatz
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05120782

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