Indole → 3-bromo-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione

HRID 388344

反応式

HRID 388344 の反応式
C1([C@H]2[C@H](C3C4C(=CC=CC=4)NC=3)C(=O)NC2=O)C2=C3C(=CC=C2)CCCN3C=1.[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30]1.[Br:38][C:39]1[C:40](=[O:52])[N:41]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:42](=[O:45])[C:43]=1Br.C[Mg]Br>>[Br:38][C:39]1[C:40](=[O:52])[N:41]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:42](=[O:45])[C:43]=1[C:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:29][CH:30]=1

参加物

5

反応物 4

HCID 798IndoleHCID 11494412TivantinibHCID 130592683,4-Dibromo-1-phenyl-1H-pyrrole-2,5-dioneHCID 178418573HCID 178418573、化合物

生成物 1

HCID 670170683-bromo-4-(1H-indol-3-yl)-1-phenyl-pyrrole-2,5-dione

実験手順

(±)-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.

出典と根拠

ORDレコード
ord-3439f193e57748c8b3cd9576cf378821
出典データセット
uspto-grants-2013_02
特許番号
US08377927B2

関連ノート

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