Methyl iodide → HCID 46947167, compound

HRID 454804Notes

Reaction equation

HRID 454804 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.O1CCCC1.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:23][C:24]3[CH:30]=[C:29]([O:31][CH2:32][CH2:33][F:34])[CH:28]=[CH:27][C:25]=3[CH:26]=2)=[CH:18][CH:17]=1>O>[CH3:14][N:15]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2[S:23][C:24]3[CH:30]=[C:29]([O:31][CH2:32][CH2:33][F:34])[CH:28]=[CH:27][C:25]=3[CH:26]=2)=[CH:20][CH:21]=1)[CH3:1]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 46947163HCID 46947163, compound

Product 1

HCID 46947167HCID 46947167, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (35 mg, 0.245 mmol) and iodomethane (CH3I, 21 μL, 0.330 mmol) were added to an anhydrous tetrahydrofuran (5 mL) solution having the 2-[4-(N-monomethylamino)phenyl]-6-(2-fluoroethoxy)benzothiophene (1-12, 50 mg, 0.165 mmol) prepared in Example 12 dissolved therein, and stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature and water was added. Organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-[4-(N,N-dimethylamino)phenyl]-6-(2-fluoroethoxy)benzothiophene (1-16, 24 mg, 46%). The obtained target compound 1-16 had a melting point of 183.9-195.9° C., and the following physical data;

Workup

  1. customprepared in Example 12
  2. dissolutiondissolved
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionOrganic compounds were extracted with ethyl acetate
  5. customevaporated after a treatment with sodium sulfate
  6. customPurification

Sources & evidence

ORD record
ord-5a43878dd34c4c4e9c82c5d8f11ff2bc
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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