4-Chloro-3-methylphenol → HCID 86610739, compound

HRID 2109335Notes

Reaction equation

HRID 2109335 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:9][C:10]1[C:11]([CH3:17])=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1.[CH3:18][N:19]([CH3:36])[C:20]([O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C@@H:29]([CH2:33][CH2:34]Br)[NH:28][CH2:27][CH2:26]2)=[O:21].[F:37][C:38]([F:43])([F:42])[C:39]([NH2:41])=[O:40]>CN(C)C=O.O>[CH3:18][N:19]([CH3:36])[C:20]([O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C@@H:29]([CH2:33][CH2:34][O:16][C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[C:11]([CH3:17])[CH:12]=1)[NH:28][CH2:27][CH2:26]2)=[O:21].[F:37][C:38]([F:43])([F:42])[C:39]([NH2:41])=[O:40]

Participants

7

Reactant 4

HCID 17324-Chloro-3-methylphenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 86610737HCID 86610737, compound

Product 1

HCID 86610739HCID 86610739, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of potassium carbonate (115 mg, 0.83 mmol), potassium iodide (catalytic amount) and 4-chloro-m-cresol (65 mg, 0.46 mmol) in dimethylformamide (2 ml) was added a solution of 6-dimethylcarbamoyloxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (160 mg, 0.38 mmol) obtained in step (e) of Example 190 in dimethylformamide (2 ml) gradually with stirring under cooling in an ice bath. Subsequently, the resulting mixture was stirred at 100° C., and after confirming the disappearance of the starting material by thin layer chromatography, the reaction temperature was cooled to ambient temperature and water was added to the reaction mixture with stirring. The resulting mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (80:20) as the eluent to afford the title compound (154 mg, yield: 84%) as a pale yellow oil.

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringSubsequently, the resulting mixture was stirred at 100° C.
  3. stirringwith stirring
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9f6f707eb90d47e491927718cc98d8ae
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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