HCID 10782159, compound → HCID 10732494, compound

HRID 2292768Notes

Reaction equation

HRID 2292768 reaction equation
[CH3:1][C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([NH2:14])=[O:13])=[CH:8][C:7]([N+:15]([O-])=O)=[CH:6][CH:5]=2.[H][H].CO.CCOC(C)=O>C1COCC1.CCO.[Pd]>[NH2:15][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]([CH3:1])=[C:10]2[CH2:11][C:12]([NH2:14])=[O:13]

Participants

6

Reactant 3

HCID 10782159HCID 10782159, compoundHCID 21584119Ethylacetate methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 10732494HCID 10732494, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 205 mg (0.634 mmol) of 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole-3-acetamide in 30 mL of 2:1 THF/EtOH was hydrogenated at 60 psi (4218 g/cm2) of hydrogen for 4 hours using 0.1 g of Pd/C as catalyst. The catalyst was filtered and the filtrate concentrated at reduced pressure. The residue was chromatographed on silica eluting with EtOAc and then 5% MeOH/EtOAc to give 52 mg (28% yield) of 5-amino-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 175°-178° C.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated at reduced pressure
  3. customThe residue was chromatographed on silica eluting with EtOAc

Sources & evidence

ORD record
ord-ab6b377f855e4e5bbb80fe0f0dd91b0f
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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