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Dibutyl sulfide → (+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate

HRID 2099754
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2099754
[CH2:1](SCCCC)[CH2:2]CC.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Li].[CH3:17][C:18]1[C:26]2[C:22](=[CH:23][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:25]=2)[CH:21]=[C:20]([CH2:35][CH:36]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:19]=1>CCOCC>[CH2:1]([C:13]1[CH:14]=[CH:15][N:10]=[C:11]([CH:36]([CH2:35][C:20]2[CH:19]=[C:18]([CH3:17])[C:26]3[C:22](=[CH:23][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[N:25]=3)[CH:21]=2)[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:12]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11002Dibutyl sulfideHCID 69069206Ethyl 4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)but-2-enoateHCID 178506720HCID 178506720, Verbindung

Produkt 1

HCID 57794570(+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283
Diethyl Ether
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 50-mL oven-dried flask was added di-n-butylsulfide (244 mg, 1.665 mmol, 4.4 equiv) and cuprous iodide (159 mg, 0.832 mmol, 2.2 equiv) under nitrogen. Anhydrous ether (1.2 mL) was added and the suspension was cooled to 0° C. before the solution of 2-pyridinyl lithium was added via canuula. A yellowish brown precipitate was formed. After stirring at 0° C. for 20 min, the cooling bath was removed and ethyl 4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)but-2-enoate (141.7 mg, 0.378 mmol, 1.0 equiv.) in anhydrous ether (1.2 mL) was added via syringe. The solution was stirred at room temperature for 1 h. The reaction mixture was then partitioned between an aqueous ammonium hydroxide/ammonium chloride solution and ethyl acetate (upon shaking, the solids gradually dissolved to a give blue aqueous solution). The layers were separated and the organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. Flash column chromatography (5% methanol in methylene chloride) afforded the desired product (80 mg, 44%) which was carried on without farther purification. MS (ESI) 482 (MH)+.

Aufarbeitung

  1. customTo a 50-mL oven-dried flask
  2. additionwas added via canuula
  3. customA yellowish brown precipitate was formed
  4. customthe cooling bath was removed
  5. stirringThe solution was stirred at room temperature for 1 h
  6. customThe reaction mixture was then partitioned between an aqueous ammonium hydroxide/ammonium chloride solution and ethyl acetate (
  7. stirringupon shaking
  8. dissolutionthe solids gradually dissolved to a give blue aqueous solution)
  9. customThe layers were separated
  10. washthe organic layer was washed with water, brine
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1cd2ae38c71e4127a4e4d8968a47d2eb
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07569578B2

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