HCID 19101761, compound → HCID 19101763, compound

HRID 1974567Notes

Reaction equation

HRID 1974567 reaction equation
[CH3:1][C:2]1[N:3]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2>CO.O1CCOCC1.[Pd]>[NH2:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:2]1[CH3:1])=[O:27]

Participants

5

Reactant 1

HCID 19101761HCID 19101761, compound

Product 1

HCID 19101763HCID 19101763, compoundYield 88.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-[2-methyl-1-(3-nitrobenzoyl)indol-3-yl]butyric acid (600 mg) in a mixture of methanol (30 ml) and 1,4-dioxane (30 ml) was added 10% palladium on activated carbon (300 mg), and the mixture was stirred under hydrogen atmosphere (3 atm) at 20° C. for 45 minutes. The catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on a silica gel column (25 ml) eluting with a mixture of chloroform and methanol (10:1) to give 4-[1-(3-aminobenzoyl)-2-methylindol-3-yl]butyric acid (490 mg) as a yellow foam.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on a silica gel column (25 ml)
  4. washeluting with a mixture of chloroform and methanol (10:1)

Sources & evidence

ORD record
ord-a5307981bed04151a53dccfd6bad5d90
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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