Potassium Iodide → 3-(4-Benzyloxy-2-chloro-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol

HRID 1097874Notes

Reaction equation

HRID 1097874 reaction equation
[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:17][C:18]1[CH:19]=[C:20]([OH:39])[CH:21]=[CH:22][C:23]=1[CH:24]([CH3:38])[C:25]([OH:37])([C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=1)[C:26]([F:29])([F:28])[F:27]>CC(C)=O>[CH2:9]([O:39][C:20]1[CH:21]=[CH:22][C:23]([CH:24]([CH3:38])[C:25]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=2)([OH:37])[C:26]([F:27])([F:28])[F:29])=[C:18]([Cl:17])[CH:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 252541463-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol

Product 1

HCID 252541473-(4-Benzyloxy-2-chloro-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-olYield 22.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium iodide (4 mg, 0.02 mmol), potassium carbonate (45 mg, 0.33 mmol), and benzyl chloride (41 mg, 0.33 mmol) were added to a solution of 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenol (Example 73, 50 mg, 0.14 mmol) in acetone (3 mL), and the mixture was refluxed for 3.5 h. The green suspension was filtered, the solvent evaporated, and the title compound (14 mg) was isolated from the residue by reversed-phase, preparative HPLC (Agilent Zorbax XdB-C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA[aq]). MS (m/e)=436.1 (MH+).

Workup

  1. temperaturethe mixture was refluxed for 3.5 h
  2. filtrationThe green suspension was filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-b97fb64c24f64bd9bfa8730e36ad43a9
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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