HCID 67487193, compound → HCID 67487287, compound

HRID 1960384Notes

Reaction equation

HRID 1960384 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([N+:18]([O-])=O)[CH:17]=1)[NH:14][C:13]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12]2)(=[O:4])=[O:3]>[C].[Pd].O1CCCC1>[NH2:18][C:16]1[CH:17]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[C:11]2[C:15]=1[NH:14][C:13]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12]2

Participants

4

Reactant 1

HCID 67487193HCID 67487193, compound

Product 1

HCID 67487287HCID 67487287, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-[3-(methylsulfonyl)propoxy]-7-nitro-1H-indole-2-carboxylate (200 mg), 10% palladium-carbon (50% containing water, 100 mg) and tetrahydrofuran (20 mL) was subjected to catalytic reduction at room temperature under hydrogen atmosphere at normal pressure. The catalyst was filtered off, and the filtrate was concentrated. The obtained crystals were washed with hexane to give the title compound (140 mg, yield 78%) as pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane to give pale-yellow prism crystals. melting point 187-188° C.

Workup

  1. customwas subjected to catalytic reduction at room temperature under hydrogen atmosphere at normal pressure
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. washThe obtained crystals were washed with hexane

Sources & evidence

ORD record
ord-73638c5a4da843d8a25da7649d9cc97e
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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