Maleimide → 3-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanenitrile

HRID 11064

Reaktionsgleichung

Reaktionsgleichung von HRID 11064
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[N:11]([CH2:21][CH2:22][C:23]#[N:24])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2.[C:25]1(=[O:31])[NH:29][C:28](=[O:30])[CH:27]=[CH:26]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:27]2[C:28](=[O:30])[NH:29][C:25](=[O:31])[C:26]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:21][CH2:22][C:23]#[N:24])[C:10]=2[CH:9]=1

Komponenten

3

Edukt 2

HCID 10935MaleimideHCID 219807953-{2-[(E)-2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}propanenitrile

Produkt 1

HCID 867602003-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanenitrileAusbeute 80,2 %

Versuchsvorschrift

Diene (236) (1.30 g, 3.86 mmol) prepared as described in example 96 was reacted with maleimide (0.49 g) following The procedure described in example 68 and then aromatized according to the procedure described in example 70 to give crude material that was chromatographed on silica eluting with ethyl acetate/hexane (1:1). Trituration from methanol gave nitrile (237) (1.33 g, 80%) as a yellow powder, mp 287–288° C. 1H NMR δ [(CD3)2SO] 11.16 (br s, 1H), 8.53 (d, J=2.6 Hz, 1H), 8.02 (s, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.59 (m, 1H), 7.49 (m, 3H), 7.33 (dd, J=9.0, 2.6 Hz, 1H), 4.86 (t, J=6.7 Hz, 2H), 3.91 (s, 3H), 3.04 (t, J=6.7 Hz, 2H). Found: C, 65.32; H, 4.15; N, 9.60. C24H16ClN3O3.3/4H2O requires: C, 65.01; H, 3.98; N, 9.47.

Aufarbeitung

  1. customto give crude material that
  2. customwas chromatographed on silica eluting with ethyl acetate/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8450601e0b244db8a4f671e080a931b1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

Verknüpfte Notizen

Wird geladen…