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

HRID 333773Notes

Reaction equation

HRID 333773 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-fb31627b410b40968e4b9fca04c13837
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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