HCID 23091916, compound → 1-(2-Tert-butoxy-2-oxoethyl)-1H-indole-5-carboxylic acid

HRID 1393671Notes

Reaction equation

HRID 1393671 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([O:20]CC3C=CC=CC=3)=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 23091916HCID 23091916, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 230919311-(2-Tert-butoxy-2-oxoethyl)-1H-indole-5-carboxylic acidYield 111.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The benzyl 1-t-butoxycarbonylmethyl-1H-indole-5-carboxylate (800 mg) obtained above was dissolved in ethanol, then 5% palladium on carbon (160 mg) was added thereto, and the mixture was stirred overnight at room temperature in a hydrogen atmosphere. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (670 mg, Y.:quant.).

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-44b9d00664d843e1a9709f53736bbbcb
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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