Potassium Iodide → 5-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester

HRID 908939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908939
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]#[N:26].[I-].[K+]>CC(C)=O.CN(C)C=O>[C:25]([CH2:24][O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)#[N:26]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 123571275-(1H-indol-3-yl)pentanoic acid

Produkt 1

HCID 673867685-(1H-Indol-3-yl)pentanoic acid cyanomethyl esterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-(1H-Indol-3-yl)pentanoic acid (5 g, 23 mmol) was dissolved in a mixture of acetone (25 ml) and dimethylformamide (25 ml), and caesium carbonate (3.75 g, 11.5 mmol), chloroacetonitrile (2.16 ml, 34.5 mmol) and potassium iodide (20 mg) were added in succession. After 6.5 h at 60° C. and 16 h at RT, the solid residues were filtered off and washed with acetone (2×30 ml) and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3). The product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g).

Aufarbeitung

  1. additionwere added in succession
  2. filtration16 h at RT, the solid residues were filtered off
  3. washwashed with acetone (2×30 ml)
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3)
  6. customThe product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g)

Quellen und Nachweise

ORD-Eintrag
ord-a61b9df88b1f4fec8b934976358ea9f2
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017630B2

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