Reaktion #11157

Reaktionsgleichung

p-toluenesulfonic acid

5-methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole

2-[(E)-2-(2-Bromo-4-nitrophenyl)ethenyl]-5-methoxy-1H-indole

2-(2-bromoethoxy)tetrahydro-2H-pyran

maleimide

→

6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product obtained
2. 2
   Sonstigewas reacted
3. 3
   Sonstigegave crude material that
4. 4
   workup.ADDITIONwas added before the solution
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   SonstigeThe organic phase was dried
7. 7
   Sonstigethe drying agent was removed
8. 8
   Einengenthe solution was concentrated to dryness
9. 9
   Sonstigechromatographed
10. 10
    Wascheneluting with ethyl acetate/hexane (1:2 to 1:1)

Vorschrift

5-methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole (II; Ar=phenyl) (1.93 g, 7.74 mmol was reacted with 2-(2-bromoethoxy)tetrahydro-2H-pyran using the procedure described in example 38. This material was reacted directly with maleimide (0.79 g) using the procedure described in method 4. The product obtained was reacted using the procedure described in example 70 gave crude material that was then dissolved in methanol (100 mL) to which p-toluenesulfonic acid (30 mg) was added before the solution was warmed to 50° C. for 3h. The solution was then 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 before being adsorbed onto silica and chromatographed eluting with ethyl acetate/hexane (1:2 to 1:1) to give 6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=phenyl, R10═(CH2)2OH) (201) in a yield of 0.51 g, 17% as a yellow powder; mp 262–264° C. 1H NMR δ [(CD3)2SO] 11.09 (br s, 1H), 8.56 (d, J=2.6 Hz, 1H), 7.83 (s, 1H), 7.66 (m, 3H), 7.47 (m, 3H), 7.28 (dd, J=9.0, 2.6 Hz, 1H), 4.86 (t, J=5.5 Hz, 1H), 4.55 (t, J=5.3 Hz, 2H), 3.90 (s, 3H), 3.78 (m, 2H). Found: C, 71.47; H. 4.77; N, 7.32. C23H18N2O4 requires: C, 71.49; H, 4.70; N, 7.25.

Quelle