HCID 67487193, compound → HCID 67487287, compound

HRID 1994818Notes

Reaction equation

HRID 1994818 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-08c6dc1978f847cf9cbe25cbabe6c87c
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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