Reaktion #43293

Reaktionsgleichung

2-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol

→

solid

Ausbeute 39.0%

2-[(2-Amino-6-{[2-(2-chlorophenyl)-5-(4-propoxyphenyl)-1H-pyrrol-1-yl]methyl}pyridine-3-yl)oxy]ethanol

Ausbeute 39.0%

Lösungsmittel

ethanol acetic acid

NaHCO3

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   Extraktionextracted twice with CH2Cl2
3. 3
   TrocknenThe combined organic layers were dried (Na2SO4)
4. 4
   Sonstigethe solvents removed under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography

Vorschrift

To a solution of 0.1 gm (0.2 mmol) of 2-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol in 4 mL of 1:1 ethanol-acetic acid was added 0.55 gm of Fe powder. The reaction mixture was allowed to stir at 96° C. for 2 h. The mixture was cooled and poured in 100 mL of saturated NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvents removed under reduced pressure. The residue was purified by column chromatography using 1%-2% methanol-chloroform-0.5% Et3N as an eluent to yield 0.037 gm (39% yield) of a solid mp 89-92° C. 1H NMR (500 MHz, CDCl3) δ: 1.00 (t, 3H, J=7.4 Hz), 1.23 (br s, 3H), 1.77 (m, 2H), 3.88 (m, 4H), 3.98 (t, 2H, J=4.3 Hz), 4.99 (s, 2H), 5.65 (d, 1H, J=8.05 Hz), 6.29 (s, 2H), 6.72 (d, 1H, J=8.05 Hz), 6.84 (d, 1H, J=8.78 Hz), 7.21 (m, 2H), 7.25 (m, 3H), 7.36 (m, 1H); MS (ES) m/z 478.2 ([M+H]+).

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