2,3-bis(5-fluoro-1H-indol-3-yl)-N-methylmaleimide → HCID 18505440, compound

HRID 1357098Notes

Reaction equation

HRID 1357098 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[C:12]([N:14]([CH3:28])[C:15](=[O:27])[C:16]=1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=2)[NH:19][CH:18]=1)=[O:13]>CN(C=O)C.[C].[Pd]>[F:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:16]1[CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)[C:12](=[O:13])[N:14]([CH3:28])[C:15]1=[O:27]

Participants

4

Reactant 1

HCID 111880732,3-bis(5-fluoro-1H-indol-3-yl)-N-methylmaleimide

Product 1

HCID 18505440HCID 18505440, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-bis(5-fluoro-1H-indol-3-yl)-N-methylmaleimide (60 mg, 0.16 mmol) in DMF (3 mL) was added a small amount of 10% palladium-carbon, and the whole was stirred at room temperature for 1 day under hydrogen atmosphere. The palladium-carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=2:1) to obtain 3,4-bis(5-fluoro-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine (58.8 mg, 97.5%) as pale red solids. 1H-NMR(CDCl3): δ 3.11(s, 3H), 4.90(s, 2H), 6.74(dt, J=2.5, 9.0 Hz, 2H), 6.99(d, J=2.5 Hz, 2H), 7.01(dd, J=9.0, 2.5 Hz, 2H), 7.09(dd, J=9.0,4.6 Hz, 2H), 10.77(br s, 2H). IR(KBr): 3420, 1700, 1490, 1440, 1295, 940, 800 cm−1. MS m/z: 379(M+).

Workup

  1. customThe palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=2:1)

Sources & evidence

ORD record
ord-97a139270e28423786ea385b5d129c87
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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