Reaktion #590556

Reaktionsgleichung

Water

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

SnCl2

→

2-(pyridin-2-yl)-1H-indol-5-amine

Ausbeute 20.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux for 10 h
3. 3
   Extraktionthe mixture was extracted with EtOAc (50 mL×3)
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Einengenconcentrated in vacuum
7. 7
   SonstigeThe residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether)

Vorschrift

To a solution of 5-nitro-2-(pyridin-2-yl)-1H-indole (700 mg, 2.9 mmol) in EtOH (20 mL) was added SnCl2 (2.6 g, 12 mmol). The mixture was heated at reflux for 10 h. Water was added and the mixture was extracted with EtOAc (50 mL×3). 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 2-(pyridin-2-yl)-1H-indol-5-amine (120 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 9.33 (brs, 1H), 8.55 (dd, J=1.2, 3.6 Hz, 1H), 7.76-7.67 (m, 2 H), 7.23 (d, J=6.4 Hz, 1H), 7.16-7.12 (m, 1H), 6.94 (d, J=2.0 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.71-6.69 (dd, J=2.0, 8.4 Hz; 1H).

Quelle