Potassium Iodide → HCID 69642248, compound

HRID 890443Notes

Reaction equation

HRID 890443 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].Cl[CH2:18][C:19]1[C:20]([CH:35]2[CH2:37][CH2:36]2)=[N:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[N:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:18][C:19]3[C:20]([CH:35]4[CH2:37][CH2:36]4)=[N:21][C:22]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=4)=[N:23][CH:24]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 219359605-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Product 1

HCID 69642248HCID 69642248, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (example 6 b]; 50 mg, 0.23 μmol), 5-chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 3 d]; 78 mg, 0.25 μmol), cesium carbonate (82 mg, 0.25 μmol) and a trace of potassium iodide were suspended in acetone (5 ml). The suspension was stirred at ambient temperature for 72 h, the solvent was 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 with ethyl acetate. The combined organic layers were washed two times with brine/ice water 1/1 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 71 mg (0.14 μmol, 63%) of the title compound as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-d51cd1e1f53c4bc0ba4f87a442dddc6b
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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