HCID 68495256, compound → HCID 68493807, compound

HRID 1038753Notes

Reaction equation

HRID 1038753 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:23][O:24][CH3:25])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15]CC1C=CC=CC=1)[CH:9]=2)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:23][O:24][CH3:25])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 68495256HCID 68495256, compound

Product 1

HCID 68493807HCID 68493807, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-benzyloxy-1-methoxymethyl-1H-indole-2-carboxylic acid ethyl ester (3.45 g, 10 mmol) in EtOH (35 ml) was added 10% Pd/C (0.35 g) and the mixture was stirred under a hydrogen atmosphere (1 atm) for 2 hours at 50° C. The catalyst was filtered off and the filtrate was evaporated. The residue was purified by silica gel column chromatography (n-hexane:AcOEt=4:1) to give 2.0 g of the title compound as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by silica gel column chromatography (n-hexane:AcOEt=4:1)

Sources & evidence

ORD record
ord-33c36fc73d3a4e2a8d0131d564203477
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

Loading…