Water → 2-tert-butyl-5-nitro-1H-indole-4-carbonitrile

HRID 468503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468503
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11](F)[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].[C-:18]#[N:19].[K+].O>CS(C)=O>[C:1]([C:5]1[NH:6][C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([C:18]#[N:19])[C:12]=2[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 9032Potassium CyanideHCID 534211832-Tert-butyl-4-fluoro-5-nitro-1H-indole

Produkt 1

HCID 591295222-tert-butyl-5-nitro-1H-indole-4-carbonitrileAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-tert-butyl-4-fluoro-5-nitro-1H-indole (4.0 g, 17 mmol) in DMSO (30 mL) was added KCN (3.4 g, 51 mmol). The mixture was stirred at 70° C. for 3 hours, and poured into water (80 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (7% EtOAc in petroleum ether) to afford 2-tert-butyl-5-nitro-1H-indole-4-carbonitrile (2.2 g, 53%). 1H NMR (DMSO, 300 MHz) δ 12.23 (br s, 1H), 8.09 (d, J=9.0 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 6.50 (s, 1H), 1.38 (s, 9H). MS (ESI) m/z: 244.2 [M-41].

Aufarbeitung

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel (7% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-b738f50fcb7144538cd76d228d5d9bf7
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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