Trimethylsilylacetylene → 2-(5-Trimethylsilanylethynyl-indol-1-yl)-ethanol

HRID 1916707

Reaktionsgleichung

Reaktionsgleichung von HRID 1916707
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:5]2.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>C(N(CC)CC)C.C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][Si:16]([C:14]#[C:15][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:5]2)([CH3:19])[CH3:18]

Komponenten

7

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 457893802-(5-Iodo-indol-1-yl)-ethanol

Produkt 1

HCID 673645732-(5-Trimethylsilanylethynyl-indol-1-yl)-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

398 mg (2.1 mmol) CuI and 1.47 g (2.1 mmol) Pd(PPh3)2Cl2 are added to a solution, cooled to 0° C., of 30 g (104 mmol) 2-(5-iodo-indol-1-yl)-ethanol and 18 mL (125 mmol) ethynyl-trimethyl-silane in 480 mL triethylamine and 120 mL THF and stirred for 30 min at 0° C. and 2 h at RT. The mixture is evaporated down i. vac., the residue is taken up in 300 mL EtOAc, the organic phase is washed with 150 mL water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1).

Aufarbeitung

  1. customThe mixture is evaporated down i
  2. washthe organic phase is washed with 150 mL water
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f39630562004788afc88eab2ed230ba
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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