Ethylene Glycol → 4-[4-(t-Butoxycarbonyl)piperazin-1-yl]-3-(1-naphthylthio)-1H-indazole

HRID 227308

Reaktionsgleichung

Reaktionsgleichung von HRID 227308
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](I)=[N:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(O)CO.[C:34]1([SH:44])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1>C(OCC)(=O)C.[Cu]I.CC(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]([S:44][C:34]2[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=2)=[N:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 682591-NaphthalenethiolHCID 178452228HCID 178452228, Verbindung

Produkt 1

HCID 589047834-[4-(t-Butoxycarbonyl)piperazin-1-yl]-3-(1-naphthylthio)-1H-indazoleAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-(t-butoxycarbonyl)piperazin-1-yl]-3-iodo-1H-indazole (0.068 g, 0.159 mmol), copper(I) iodide (0.005 g, 0.024 mmol) and potassium carbonate (0.044 g, 0.318 mmol) are added to a screw-capped test tube with a Teflon-lined septum. The tube is evacuated and backfilled with argon and this procedure repeated twice more. The reaction mixture is treated sequentially with 2-propanol (1.5 mL), ethylene glycol (19 μL, 0.318 mmol) and 1-naphthalenethiol (0.051 g, 0.318 mmol), heated at 130°-140° C. for 8 h, cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure. The resultant crude material is purified by flash chromatography (silica gel, 40:60 ethyl acetate/hexanes) to afford the title compound as a colorless oil, 0.033 g (45% yield), identified by NMR and mass spectral analyses.

Aufarbeitung

  1. customThe tube is evacuated
  2. temperatureheated at 130°-140° C. for 8 h
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customThe resultant crude material is purified by flash chromatography (silica gel, 40:60 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-306fa838894a4c9a85c2abf0057dcb50
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560470B2

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