Indole-3-acetamide → 3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

HRID 1465914Notes

Reaction equation

HRID 1465914 reaction equation
[C:1]1([C:13](=O)[C:14](OC)=[O:15])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][C:29]([NH2:31])=[O:30])=[CH:20]1>>[C:1]1([C:13]2[C:14](=[O:15])[NH:31][C:29](=[O:30])[C:28]=2[C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

3

Reactant 2

HCID 397Indole-3-acetamide2×HCID 59298805methyl 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxoacetate2×

Product 1

HCID 99692093-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Procedure

In one embodiment, the method of the present invention comprises a step of dissolving methyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl-oxoacetate and indole-3-acetamide in an organic solvent and adding the obtained solution to a base, and reacting methyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl-oxoacetate and indole-3-acetamide to form highly pure 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione. In one embodiment, the base is dissolved or suspended in an organic solvent. In a further embodiment, the base is dissolved or suspended in the same organic solvent as methyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl-oxoacetate and indole-3-acetamide. In a further embodiment, highly pure 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrolidine-2,5-dione is formed by reducing 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione.

Workup

  1. additionadding the obtained solution to a base

Sources & evidence

ORD record
ord-569cca18541743f39a0792b8de528f85
Source dataset
uspto-grants-2015_04
Patent number
US09000005B2

Reaction notes

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