5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide → HCID 24804767, compound

HRID 16634Notes

Reaction equation

HRID 16634 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]CC3C=CC=CC=3)[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[CH3:32])=[O:8]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[CH3:32])=[O:8]

Participants

3

Reactant 1

HCID 589447245-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide2×

Product 1

HCID 24804767HCID 24804767, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide (Compound 56, 0.15 g, 0.31 mmol) in methanol (15 ml), which was degassed with argon for 10 min, was added 10% palladium on carbon (0.17 g), with continued degassing. The reaction was placed in par tube on hydrogenator and hydrogenated at 45 psi for 18 h. The reaction was then filtered, concentrated under reduced pressure and the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes) to yield 5-hydroxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide (Compound 29) as a solid (0.11 g, 92%).

Workup

  1. customwas degassed with argon for 10 min
  2. additionwas added 10% palladium on carbon (0.17 g)
  3. filtrationThe reaction was then filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b67d2a2af3e84a65b22ba81bd6e15ab7
Source dataset
uspto-grants-2010_06
Patent number
US07737173B2

Reaction notes

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