Reaktion #11156

Reaktionsgleichung

BBr3

4-(2-Chlorophenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

NaHCO3

water

example 40

5-Methoxy-2-[2-(3,5-dinitrophenyl)ethenyl]-1H-indole

→

4-(2-Chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

VI

9-hydroxy-4-(2-methoxy-5-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   SonstigeThe organic phase was dried
3. 3
   Sonstigethe drying agent was removed
4. 4
   Einengenthe solution was concentrated to dryness
5. 5
   Sonstigechromatographed
6. 6
   WaschenElution with ethyl acetate/petroleum ether (1:1)

Vorschrift

A solution of 1N BBr3 in CH2Cl2 (11.5 mL, 0.011 mol) was added to a solution of 4-(2-Chlorophenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chlorophenyl, R10═CH2CH2CH2OH) (31) prepared as described in example 40 (1.00 g, 2.30 mmol) in CH2Cl2 under nitrogen and the reaction mixture was stirred at room temperature for 3 h. Saturated aqueous NaHCO3 solution was added and the solution was diluted with water and extracted with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness, adsorbed onto silica and chromatographed. Elution with ethyl acetate/petroleum ether (1:1) followed by ethyl acetate gave 4-(2-Chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chlorophenyl, R10═CH2CH2CH2OH) (34) in a yield of 0.90 g, 93%, which crystallised from THF/petroleum ether as a yellow/orange powder, mp 291–294° C. 1H NMR δ [(CD3)2SO 11.05 (br s, 1H), 9.36 (s, 1H), 8.38 (d, J=2.5 Hz, 1H), 7.74 (s, 1H), 7.59–7.54 (m, 2H), 7.52–7.42 (m, 3H), 7.14 (dd, J=8.7, 2.5 Hz, 1H), 4.62 (br t, 1H), 4.49 (t, J=6.8 Hz, 2H), 3.41 (m, 2H), 1.90 (m, 2H). Found: C, 64.99; H, 4.13; N, 6.43. C23H17ClN2O4.1/4H2O requires C, 64.94; H, 4.15; N, 6.58.

Quelle