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Tetrabutylammonium Fluoride → 3-[2-(3-Hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276952
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 276952
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([C:22]3[C:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=34)=[N:16]2)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([C:22]3[C:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=34)=[N:16]2)[CH2:10]1
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Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 226291913-[2-{3-(Tert-butyldimethylsilyloxy)cyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Produkt 1

HCID 226292043-[2-(3-Hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A solution of 3-[2-{3-(tert-butyldimethylsilyloxy)cyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (570 mg) and 70% aqueous tetrabutylammonium fluoride (4.3 g) in tetrahydrofuran (10 ml) was stirred for overnight at room temperature. A reaction mixture was diluted with ethyl acetate (100 ml), which was washed in turn with water (50 ml×4) and saturated sodium chloride in water (50 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (40 ml) eluting in turn with 30%, 50% ethyl acetate in dichloromethane and ethyl acetate. Fractions containing desired product were concentrated under reduced pressure to give residue, which was recrystallized from ethanol to give 3-[2-(3-hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (430 mg).

Aufarbeitung

  1. washwas washed in turn with water (50 ml×4) and saturated sodium chloride in water (50 ml×2)
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (40 ml)
  6. washeluting in turn with 30%, 50% ethyl acetate in dichloromethane and ethyl acetate
  7. additionFractions containing desired product
  8. concentrationwere concentrated under reduced pressure
  9. customto give residue, which
  10. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1b3b5652a39547f282010dcdcbdd20e1
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06355640B1

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