HCID 59344934, compound → HCID 59344919, compound

HRID 18171Notes

Reaction equation

HRID 18171 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:18]CC3C=CC=CC=3)[CH:13]=[C:14]([F:17])[CH:15]=2)[CH:10]=[C:9]1[C:26]([NH2:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([OH:18])[CH:13]=[C:14]([F:17])[CH:15]=2)[CH:10]=[C:9]1[C:26]([NH2:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59344934HCID 59344934, compound

Product 1

HCID 59344919HCID 59344919, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-benzyloxy-6-fluoro-1H-indole-2-carboxylic acid amide (570 mg, 1.52 mmol) in EtOH (20 ml) was added to a Parr vessel containing catalytic amount of 5% Pd on carbon. The vessel was purged with H2 at the pressure of 3.45 Bar. After shaking overnight, the reaction mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by flash chromatography to give 1-benzyl-6-fluoro-4-hydroxy-1H-indole-2-carboxylic acid amide as yellow solid (312 mg, 72%). MS: 285.2 (M+H)+.

Workup

  1. customThe vessel was purged with H2 at the pressure of 3.45 Bar
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-36215371ac8249918f8d1ce696923ead
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

Loading…