Sodium Chloride → HCID 59536218, compound

Participants

Reaction Conditions

Reaction Steps

2-[4-(N-Monomethylamino)phenyl]-6-[2-(t-butyldimethylsilyloxy)ethoxy]benzothiophene (115, 150 mg, 0.36 mmol) obtained in Example 56 was dissolved in dimethylformamide (5 mL) and potassium carbonate (75 mg, 0.54 mmol) and iodomethane (0.23 mL, 0.36 mmol). The reaction mixture was stirred at 80° C. for 12 hours and an aqueous solution of sodium chloride and water were added to the reaction mixture and organic compounds were extracted with dichloromethane and extracted with ethyl acetate. The recovered organic solution was washed with a brine solution and dried over sodium sulfate to remove water and the solvent was removed under reduced pressure. The resulting mixture was dissolved in tetrahydrofuran (5 mL) and tetrabutylammonium fluoride (TBAF) (143 mg, 0.54 mmol) was added and stirred at room temperature for 30 minutes. Water was added to the reaction mixture and organic compounds were extracted with ethyl acetate. The recovered organic solution was washed with a saturated aqueous solution of sodium chloride and dried over sodium sulfate to remove water. Purification was performed by column chromatography to give 2-[4-(N,N-dimethylamino)phenyl]-6-(2-hydroxyethoxy)benzothiophene (118, 96 mg, 85%) as a white solid. The obtained target compound 118 had a melting point of 205-206° C., and the following physical data;

Provenance & Evidence