Water → 3-[1-(4-Aminomethyl-3-hydroxybenzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]-pyrrole-2,5-dione

HRID 1859200Notes

Reaction equation

HRID 1859200 reaction equation
[NH2:1][CH2:2][C:3]1[CH:35]=[CH:34][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=3[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)=[CH:9]2)=[CH:5][C:4]=1[O:36]COCC[Si](C)(C)C.O.FC(F)(F)C(O)=O.C(OCC)(=O)C.C(O)C.[OH-].[NH4+]>C(Cl)Cl.C(OCC)(=O)C>[NH2:1][CH2:2][C:3]1[CH:35]=[CH:34][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=3[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)=[CH:9]2)=[CH:5][C:4]=1[OH:36]

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 18433202Ethyl acetate ethanol ammonium hydroxideHCID 221232973-[1-(4-Aminomethyl-3-(2-(trimethylsilyl)ethoxymethoxy)benzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]pyrrole-2,5-dione

Product 1

HCID 221232753-[1-(4-Aminomethyl-3-hydroxybenzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]-pyrrole-2,5-dioneYield 22.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 10 (0.068 g, 0.11 mmol) was dissolved in methylene chloride (0.5 ml). Water (0.1 mL) was added and the solution cooled on ice. Trifluoroacetic acid (1 mL) was added and the reaction allowed to proceed for 30 minutes. Extractive workup with ethyl acetate followed by chromatography (ethyl acetate/ethanol/ammonium hydroxide:90/10/2) yields 3-[1-(4-aminomethyl-3-hydroxybenzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]-pyrrole-2,5-dione (0.012 g,) as a red solid. Treatment with hydrochloric acid yields the title compound.

Workup

  1. temperaturethe solution cooled on ice

Sources & evidence

ORD record
ord-527ae99b34e54cc4a24e99c1efe1da9d
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Reaction notes

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