2-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol → HCID 57421256, compound

HRID 1097875Notes

Reaction equation

HRID 1097875 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([OH:30])([CH:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[CH3:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>C(OCC)(=O)C>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[CH:20]([CH3:21])[C:15]([C:13]1[CH:12]=[CH:11][NH:10][C:9](=[O:8])[CH:14]=1)([OH:30])[C:16]([F:19])([F:18])[F:17]

Participants

3

Reactant 1

HCID 252538282-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 57421256HCID 57421256, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol (Example 54, 300 mg) was dissolved in ethyl acetate (10 mL) and the flask was flushed with argon. Palladium on activated charcoal (10% Pd, 75 mg) was added and the mixture was hydrogenated for 2 hours with vigorous stirring. The suspension was filtered and the catalyst was washed with methanol. The filtrate was concentrated in vacuo and the residue was dried in high vacuum to give the title compound as a light brown powder (217 mg). MS (m/e, ISP neg. ion): 364.4 (M−H+)−.

Workup

  1. customthe flask was flushed with argon
  2. additionPalladium on activated charcoal (10% Pd, 75 mg) was added
  3. filtrationThe suspension was filtered
  4. washthe catalyst was washed with methanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was dried in high vacuum

Sources & evidence

ORD record
ord-7c9b26e44bcd4392b919d1ad7262dfa3
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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