1-benzoyl-5-nitro-1H-indole → HCID 9856121, compound

HRID 1359137Notes

Reaction equation

HRID 1359137 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O1CCCC1.C([O-])=O.[NH4+].[Pd]>[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 98350711-benzoyl-5-nitro-1H-indole

Product 1

HCID 9856121HCID 9856121, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 23938PalladiumSolventHCID 2723923Ammonium formateSolvent

Conditions

Temperature
30 °C

Procedure

1-benzoyl-5-nitro-1H-indole (50 mg) was dissolved in a mixed solvent with methanol (2 ml) and tetrahydrofuran (2 ml), and ammonium formate of an excess amount and palladium/carbon (10%) of a catalytic amount were added. The reacted solution was stirred at around 30° C. for 30 minutes to complete the reduction, filtered through celite and then, concentrated under reduced pressure. Afterward, the residue was dissolved again in ethylacetate (10 ml), washed with water and brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and then, triturated with isooctane and isopropyleter. As a result, the present compound (25 mg, productive yield 56%) was obtained as a solid.

Workup

  1. additionwere added
  2. filtrationfiltered through celite
  3. concentrationconcentrated under reduced pressure
  4. dissolutionAfterward, the residue was dissolved again in ethylacetate (10 ml)
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customtriturated with isooctane and isopropyleter
  9. customAs a result, the present compound (25 mg, productive yield 56%) was obtained as a solid

Sources & evidence

ORD record
ord-419943ebf2e0475d976431e20c35e3fa
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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