HCID 58288500, compound → HCID 58288488, compound

HRID 1969049Notes

Reaction equation

HRID 1969049 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]=[N+]=[N-])[CH:7]=1)[CH3:2]>CCO>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:14]=2[CH2:23][NH2:24])[CH:7]=1)[CH3:2]

Participants

3

Reactant 1

HCID 58288500HCID 58288500, compound

Product 1

HCID 58288488HCID 58288488, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[3-(2-Azidomethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.187 g, 0.49 mmol) was dissolved in EtOH (6 mL), and the solution was purged with H2 under an H2 balloon. Palladium on carbon (10%; 0.038 mg) was added, and the mixture was purged again with H2. The reaction was sealed and stirred at room temperature overnight. Analytical LCMS indicated that starting material was still present, so additional palladium on carbon (10%; 0.038 g) was added, and the mixture was stirred under 65 psi of H2 using a Parr apparatus. After 6 hours, no starting material was seen by analytical LCMS, so the mixture was filtered through a pad of Celite, and the filter cake was washed with EtOH. The filtrate was concentrated to give the title compound.

Workup

  1. customthe solution was purged with H2 under an H2 balloon
  2. additionPalladium on carbon (10%; 0.038 mg) was added
  3. customthe mixture was purged again with H2
  4. customThe reaction was sealed
  5. additionso additional palladium on carbon (10%; 0.038 g) was added
  6. stirringthe mixture was stirred under 65 psi of H2 using a Parr apparatus
  7. waitAfter 6 hours
  8. filtrationwas filtered through a pad of Celite
  9. washthe filter cake was washed with EtOH
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-79a9b10236354aea854144beb255f0b8
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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