Potassium Iodide → 1H-Indole, 4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]methoxy]-

HRID 1767869Notes

Reaction equation

HRID 1767869 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.Cl[CH2:12][C:13]1[S:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[N:15][C:14]=1[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[CH3:28][C:14]1[N:15]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[S:17][C:13]=1[CH2:12][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 754211H-indol-4-olHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 115746051H-Indole, 4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]methoxy]-Yield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxyindole (100 mg, 0.75 mmol), 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (219 mg, 0.75 mmol; PCT Int. Appl. (2002), WO 0262774 A1), cesium carbonate (489 mg, 1.5 mmol) and a trace of potassium iodide were suspended in acetone (10 ml). The suspension was stirred at ambient temperature for 14 h, the solvent evaporated under reduced pressure and the residue dissolved in 1 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 130 mg (0.33 mmol, 45%) of the title compound as light yellow solid.

Workup

  1. customthe solvent evaporated under reduced pressure
  2. dissolutionthe residue dissolved in 1 N HCl/ice water 1/1
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted two times with ethyl acetate
  5. washThe combined organic layers were washed two times with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-4835145db7cd4613ba7a59e898df8707
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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