HCID 58980664, compound → HCID 58980657, compound

HRID 735789Notes

Reaction equation

HRID 735789 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:31])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[O:23]CC2C=CC=CC=2)=[O:13])[C:8]([O:32][CH3:33])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:31])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[OH:23])=[O:13])[C:8]([O:32][CH3:33])=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58980664HCID 58980664, compound

Product 1

HCID 58980657HCID 58980657, compoundYield 108.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Pd(OH)2 (20% on C, 24 mg) was added to a solution of the above indole (231 mg, 0.52 mmol) in ethanol/ethyl acetate (3:2, 5.0 mL) at room temperature. The solution was placed under a hydrogen atmosphere (1 atm) and stirred at room temperature for 18 h. The mixture was filtered through diatomaceous earth and concentrated in vacuo to provide 7-hydroxy-1-methyl-1H-indole-2-carboxylic acid (2-tert-butyl-5-methoxy-pyridin-4-yl)-amide (199 mg, 99%) as a pale brown solid.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5385f28e8ac48ff996f63abcaf61e8c
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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