Reaktion #555560

Reaktionsgleichung

4-nitro-2-(pyridin-2-ylethynyl)aniline

t-BuOK

→

5-nitro-2-(pyridin-2-yl)-1H-indole

Ausbeute 67.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane (3×50 mL)
2. 2
   WaschenThe combined organic layers were washed with brine
3. 3
   Trocknendried over anhydrous Na2SO4
4. 4
   Einengenconcentrated in vacuum
5. 5
   SonstigeThe residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether)

Vorschrift

To the solution of 4-nitro-2-(pyridin-2-ylethynyl)aniline (1.5 g, 6.3 mmol) in DMF (50 mL) was added t-BuOK (1.5 g, 13 mmol). The reaction mixture was stirred at 90° C. for 2 h. The mixture was diluted with water and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford 5-nitro-2-(pyridin-2-yl)-1H-indole (1.0 g, 67% yield). 1H NMR (300 MHz, d-DMSO) δ 12.40 (s, 1H), 8.66 (d, J=2.1 Hz, 1H), 8.58 (d, J=1.8 Hz, 1H), 8.07-7.91 (m, 3H), 7.59 (d, J=6.6 Hz, 1H), 7.42-7.37 (m, 2H).

Quelle