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3-[2-(2-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine → 3-[2-(2-Methylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 965359
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 965359
[CH3:1]C(C)([O-])C.[K+].O=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([C:21]2[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:23][N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=23)=[N:15]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:1]=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([C:21]2[C:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[N:23][N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=23)=[N:15]1
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Komponenten

5

Edukt 2

HCID 110690413-[2-(2-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 226292583-[2-(2-Methylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a stirred suspension of methyltriphenylphosphonium bromide (1.39 g) in tetrahydrofuran (30 ml) was added potassium tert-butoxide (437 mg) under nitrogen atmosphere at 0° C. After the mixture was stirred at 0°-5° C. for 1.5 hours, to this was added a solution of 3-[2-(2-oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (500 mg) in tetrahydrofuran (10 ml). The mixture was stirred at room temperature for 4 hours and stood at room temperature overnight. Insoluble materials were filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane (30 ml). The dichloromethane solution was washed with brine (20 ml), dried over anhydrous sodium sulfate, and evaporated in vacuo. The crude material was purified by column chromatography on silica gel using dichloromethane as an eluant to give colorless crystals of 3-[2-(2-methylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (186 mg).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. waitstood at room temperature overnight
  3. filtrationInsoluble materials were filtered off
  4. customthe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (30 ml)
  6. washThe dichloromethane solution was washed with brine (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo
  9. customThe crude material was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-912cb31cefcb4a1fbee0bdf464c6031c
Quelldatensatz
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05773530

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