HCID 11016392, compound → HCID 9847078, compound

HRID 1859197Notes

Reaction equation

HRID 1859197 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:35]=[CH:36][CH:37]=1)[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[C:19](=[O:34])[NH:20][C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:10]1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C.C(OCC)(=O)C>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:35]=[CH:36][CH:37]=1)[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[C:19](=[O:34])[NH:20][C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:10]1

Participants

5

Reactant 1

HCID 11016392HCID 11016392, compound

Product 1

HCID 9847078HCID 9847078, compound

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A dispersion of Lindlar catalyst (0.150 g) in ethanol (10 ml) was hydrogenated at atmospheric pressure for 15 min. Then, a solution of the product of step c) (0.187 g, 0.38 mmol) in ethyl acetate (3 mL) was added with a syringe, and the resulting mixture stirred vigorously for 45 h. The solution was filtered through Celite® (a silica gel) and the solvents evaporated. Chromatography on silica (ethyl acetate/methanol/ammonium hydroxide; 80/20/2; v/v) furnished 20.1 mg of 3-[1-(3-aminomethylbenzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-pyrrole-2,5-dione which was dissolved in ethanolic HCl (1.5 M), evaporated, dissolved in methanol, evaporated to dryness, dissolved in water and freeze dried to afford the title compound.

Workup

  1. filtrationThe solution was filtered through Celite® (a silica gel) and the solvents
  2. customevaporated

Sources & evidence

ORD record
ord-be80a54d19ee4b528a29de216f0480aa
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Reaction notes

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