HCID 23091903, compound → 1-(Hydroxymethyl)-1H-indole-5-carboxylic acid

HRID 1393668Notes

Reaction equation

HRID 1393668 reaction equation
C([O:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

5

Reactant 2

HCID 23091903HCID 23091903, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 230919831-(Hydroxymethyl)-1H-indole-5-carboxylic acidYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 1-benzyloxymethyl-1H-indole-5-carboxylic acid (380 mg) obtained in Intermediate Example 47 was suspended in ethanol (6.5 ml). 10% Palladium on carbon (190 mg) was added thereto and stirred for 47 hours at 60° C. in a hydrogen atmosphere. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 50:1) to give the title compound (120 mg, Y.:48%).

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 50:1)

Sources & evidence

ORD record
ord-793c1de225ff4695bfb894c7d9bbe8d1
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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