Methanol → N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide

HRID 351905Notes

Reaction equation

HRID 351905 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[O:22]CC2C=CC=CC=2)[NH:15][CH:14]=1)=[O:12].CO.[H][H]>[Pd].C(O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[OH:22])[NH:15][CH:14]=1)=[O:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 15337623HCID 15337623, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15337630N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-Fluoro-4-methoxyphenyl)-4-benzyloxy-1H-indole-3-carboxamide (1.34 g, 3.4 mmol), prepared using the method above, was slurried with 10% palladium on carbon (134 mg) in ethanol (35 mL) in a Parr bottle and placed under a hydrogen atmosphere (50 psi) for 5 h. Methanol (5 ml) was added and the mixture returned to the Hydrogen atmosphere for an additional 18 h. The solution was filtered through Celite, concentrated in vacuo, and the residue purified by flash chromatography to afford N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide (Compound 2) as a beige solid; mp 259-261° C. (d).

Workup

  1. customfor 5 h
  2. filtrationThe solution was filtered through Celite
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-4ae707abd50b47c687f3a472e514fad0
Source dataset
uspto-grants-2004_06
Patent number
US06743817B2

Reaction notes

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