HCID 18403494, compound → HCID 18403521, compound

HRID 1453641Notes

Reaction equation

HRID 1453641 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[C:13](=[O:27])[NH:14][C:15](=[O:26])[C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)=[CH:3]1>[Pd].CC(O)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[C:13](=[O:27])[NH:14][C:15](=[O:26])[C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=2)=[CH:3]1

Participants

4

Reactant 1

HCID 18403494HCID 18403494, compound

Product 1

HCID 18403521HCID 18403521, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(1-methyl-5-chloroindol-3-yl)-4-(3-nitrophenyl)-1H-pyrrole-2,5-dione (865 mg), 10% palladium on carbon (90 mg), and glacial HOAc (35 mL) was stirred and hydrogenated at atmospheric pressure using a balloon (2 h). The reaction mixture was filtered through a pad of celite, cooled to 0° C. and KOH pellets were added until pH 8. The solution was extracted with ETOAc, dried (magnesium sulfate), and stripped. The crude was flash chromatographed with 10% through 20% ETOAc-Hexane to provide 3-(1-methyl-5-chloroindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (495 mg).

Workup

  1. customa balloon (2 h)
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. additionKOH pellets were added until pH 8
  4. extractionThe solution was extracted with ETOAc
  5. dry with materialdried (magnesium sulfate)
  6. customchromatographed with 10% through 20% ETOAc-Hexane

Sources & evidence

ORD record
ord-f413ef489c4c4f409f8585cbb8e2397a
Source dataset
uspto-grants-2009_01
Patent number
US07476676B2

Reaction notes

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