HCID 59409006, compound → HCID 59409001, compound

HRID 1894734Notes

Reaction equation

HRID 1894734 reaction equation
[CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][C:9]([C:13]4[C:14](=[O:28])[NH:15][C:16](=[O:27])[C:17]=4[C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][CH:19]=4)=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1>[Pd].CO>[CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][C:9]([C@H:13]4[C@@H:17]([C:18]5[C:26]6[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=6)[NH:20][CH:19]=5)[C:16](=[O:27])[NH:15][C:14]4=[O:28])=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

4

Reactant 1

HCID 59409006HCID 59409006, compound

Product 1

HCID 59409001HCID 59409001, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (753 mg, 2.05 mmol) and 5% palladium on carbon (100 mg) in methanol (40 ml) were stirred under hydrogen at 60 psi for 15 hours at room temperature. The reaction mixture was filtered through a bed of celite and the filtrate evaporated to dryness to afford (±)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione (760 mg) which was used without further purification. LCMS: 370 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-2f27a14aac4245b38c68ecac4071a620
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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