Allyl bromide → 6-Ally-4-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11129

Reaktionsgleichung

Reaktionsgleichung von HRID 11129
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:36])[N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=3[O:34][CH3:35])[C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:37][CH3:38])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:45](Br)[CH:46]=[CH2:47]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:47]([N:11]1[C:10]2[CH:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:20]3[C:21](=[O:36])[N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=4[O:34][CH3:35])[C:23](=[O:24])[C:19]=3[C:18]=2[C:17]2[CH:16]=[C:15]([O:37][CH3:38])[CH:14]=[CH:13][C:12]1=2)[CH:46]=[CH2:45]

Komponenten

7

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 118430084-(2-Chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Produkt 1

HCID 695854926-Ally-4-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of carbazole (287) (150 mg, 0.28 mmol) prepared as described in example 297 in dimethylformamide (10 mL) under nitrogen was added potassium carbonate (0.39 g, 2.80 mmol) and allyl bromide (720L, 0.84 mmol). The resulting suspension was warmed to 90° C. with stirring for 3 hours before being diluted with water and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetate/hexane (1:2), followed by crystallization from diethyl ether/hexane gave carbazole (288) (90 mg, 57%) as a yellow powder, mp 171–173° C. 1H NMR δ [(CD3)2SO] 8.51 (d, J=2.6 Hz, 1H), 7.84 (s, 1H), 7.67 (d, J=8.9 Hz, 1H), 7.58 (m, 1H), 7.53–7.46 (m, 3H), 7.32 (dd, J=8.9, 2.6 Hz, 1H), 6.97 (d, J=8.4 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H), 6.45 (dd, J=8.4, 2.4 Hz, 1H), 5.99 (m, 1H), 5.18 (d, J=4.9 Hz, 2H), 5.14 (dd, J=10.3, 1.3 Hz, 1H), 4.99 (dd, J=17.2, 1.3 Hz, 1H), 4.69 (s, 2H), 3.90 (s, 3H), 3.80 (s, 3H), 3.72 (s, 3H). Found: C, 69.97; H, 4.75; N, 5.12. C33H27ClN2O5 requires: C, 69.90; H, 4.80; N, 4.94.

Aufarbeitung

  1. customThe organic phase was dried
  2. customthe drying agent was removed
  3. concentrationthe solution was concentrated to dryness
  4. customChromatography on silica eluting with ethyl acetate/hexane (1:2), followed by crystallization from diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-fd3a31722eab4427bb653cfb10123b6e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

Verknüpfte Notizen

Wird geladen…