1-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraene → 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione

HRID 2234900

Reaktionsgleichung

Reaktionsgleichung von HRID 2234900
Br[C:2]1[C:3](=[O:23])[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5](=[O:16])[C:6]=1[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.[CH:24]1[C:34]2=[C:35]3[C:30](=[CH:31][CH:32]=[CH:33]2)[CH2:29][CH2:28][CH2:27][N:26]3[CH:25]=1.C[Si](C)(C)[Si](C)(C)C.[Li]>C1(C)C=CC=CC=1.C1(B(O)O)C2=C3C(=CC=C2)CCCN3C=1>[C:24]1([C:2]2[C:3](=[O:23])[N:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:5](=[O:16])[C:6]=2[C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[C:34]2=[C:35]3[C:30](=[CH:31][CH:32]=[CH:33]2)[CH2:29][CH2:28][CH2:27][N:26]3[CH:25]=1

Komponenten

6

Edukt 3

HCID 156456291-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraeneHCID 57425481Lithium hexamethyldisilaneHCID 670170683-bromo-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione

Produkt 1

HCID 670170523-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 59298795(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-boranediolLösungsmittel

Versuchsvorschrift

(±)-Trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1H-indol-3-yl)pyrrolidine-2,5-dione may be prepared by reacting 1H-indole and 3,4-dibromo-1-phenyl-pyrrole-2,5-dione in the presence of methyl magnesium bromide to yield 3-bromo-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione. The 3-bromo-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione is subsequently reacted with 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline and LiHMDS (lithium hexamethyldisilane) in toluene or (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-boranediol and Pd(PPh3)-4-(tetrakis(triphenylphosphine)palladium) to yield 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione, which is reduced and deprotected by treatment with Mg in methanol, as in Example 2 procedure C, followed by catalytic hydrogenation over palladium on carbon to yield (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1H-indol-3-yl) pyrrolidine-2,5-dione. Bnz is benzyl.

Quellen und Nachweise

ORD-Eintrag
ord-55b2d14ddb0e465490703686b6ffc12f
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713969B2

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