3-[1-(2,2-dimethyl-propionyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione → 3-(1H-Indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 1004205Notes

Reaction equation

HRID 1004205 reaction equation
CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15](=[O:33])[NH:16][C:17](=[O:32])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-:30])=[O:29])=[CH:25][CH:26]=3)[N:21]([CH3:31])[CH:20]=2)=[CH:6]1)=O.O(C)[Na]>CO>[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15](=[O:33])[NH:16][C:17](=[O:32])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-:30])=[O:29])=[CH:25][CH:26]=3)[N:21]([CH3:31])[CH:20]=2)=[CH:6]1

Participants

4

Reactant 2

HCID 154588113-[1-(2,2-dimethyl-propionyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dioneHCID 178418582HCID 178418582, compound

Product 1

HCID 98864633-(1H-Indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.7 g (3.61 mmol) of 3-[1-(2,2-dimethyl-propionyl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (4) from Step E above in 60 ml of methanol was treated with 5.6 ml (8.96 mmol) of a 1.6 molar solution of NaOCH3 in methanol. The reaction was stirred at room temperature for 1 hour, poured in 2N-HCl/ice and extracted with ethyl acetate. The organic extracts were dried on anhydrous MgSO4 and concentrated to yield, after chromatographic purification, 394.7 mg (28%) of 3-(1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (I) as a red solid mp>280° C. MS: (M+), m/z 386.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried on anhydrous MgSO4
  3. concentrationconcentrated
  4. customto yield
  5. customafter chromatographic purification, 394.7 mg (28%) of 3-(1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (I) as a red solid mp>280° C

Sources & evidence

ORD record
ord-baf1e88185524797b71dc5b066d145f0
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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