HCID 18511423, compound → HCID 18511442, compound

HRID 1370333Notes

Reaction equation

HRID 1370333 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:15]([C:17]2[C:26]3[C:21](=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:24][CH:25]=3)[N:20]=[C:19]([C:31]([F:34])([F:33])[F:32])[CH:18]=2)[OH:16])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CCO.[Pd]>[F:33][C:31]([F:32])([F:34])[C:19]1[CH:18]=[C:17]([CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[OH:16])[C:26]2[C:21](=[C:22]([C:27]([F:30])([F:28])[F:29])[CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

4

Reactant 1

HCID 18511423HCID 18511423, compound

Product 1

HCID 18511442HCID 18511442, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of α-(3-benzyloxyphenyl)-2,8-bis(trifluoromethyl)-4-quinolinemethanol (80 mg, 0.17 mmol) in EtOH (4 mL) was treated with 10% Pd/C (5 mg), hydrogenated for 2 h, filtered to remove the catalyst, concentrated in vacuo and the resulting oil purified by chromatography [SiO2; heptane-EtOAc (1:1)] to give the title compound (36 mg, 53%) as an oil: NMR δH (400 MHz, CDCl3) 5.35 (1H, br s), 6.45 (1H, s), 6.65-6.80 (2H, m), 6.91 (1H, d, J 10.0 Hz), 7.21 (1H, t, J 7.0 Hz), 7.59 (1H, t, J 9.0 Hz), 8.12 (2H, t, J 9.0 Hz) and 8.22 (1H, s).

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationconcentrated in vacuo
  4. customthe resulting oil purified by chromatography [SiO2; heptane-EtOAc (1:1)]

Sources & evidence

ORD record
ord-9a3a5025e0514dc28d867964ee1433e3
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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