Water → 3-(5-(1,3-Dioxan-2-yl)furan-2-yl)-1-(4-picolyl)indazole

HRID 2227550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2227550
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[O:11][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][N:13]=2)=[CH:9][CH:8]=1.[H-].[Na+].Cl.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1.O>CN(C=O)C.C(OCC)(=O)C>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[O:11][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:30][C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)[N:13]=2)=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 745704-(Chloromethyl)pyridinium chlorideHCID 15840328HCID 15840328, Verbindung

Produkt 1

HCID 158403293-(5-(1,3-Dioxan-2-yl)furan-2-yl)-1-(4-picolyl)indazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2 g (7.41 mmol) of 3-(5-(1,3-dioxan-2-yl)furan-2-yl)indazole in 10 ml of DMF is added to a suspension of 355 mg of NaH (60 per cent in paraffin) in 10 ml of DMF under argon, and the mixture is stirred at room temperature for 1 hour. 1.46 g of 4-picolyl chloride hydrochloride are then added, followed by 355 mg of NaH (60 percent in paraffin). The mixture is stirred at room temperature for 1 hour and then at 100° C. for 1 hour, introduced into water and extracted with ethyl acetate, the organic phase is dried with sodium sulphate and evaporated in vacuo and the residue is chromatographed over silica gel using toluene/ethyl acetate mixtures as the eluent. 1 g (37% of theory) of an oil is obtained. Rf (SiO2, ethyl acetate): 0.25

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. waitat 100° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried with sodium sulphate
  5. customevaporated in vacuo
  6. customthe residue is chromatographed over silica gel
  7. custom1 g (37% of theory) of an oil is obtained

Quellen und Nachweise

ORD-Eintrag
ord-940541aad2f5400c9cce69dd8fb58bce
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06414009B1

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