Sodium Bicarbonate → (2S)-2-{3-[5-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-pyrrol-2-yl]-5-[4-(methylsulfonyl)phenoxy]phenoxy}propan-1-ol

Participants

Reaction Conditions

Reaction Steps

2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-thiazole (88 mg, 0.18 mmol) synthesized in Example (25c) was dissolved in dichloromethane (5 mL), and cooled to −78° C., a 1.0 mol/L boron tribromide dichloromethane solution (0.22 mL, 0.22 mmol) was added under nitrogen atmosphere. After the temperature was raised naturally and the solution was stirred at room temperature for 1 hour, subsequently a saturated aqueous sodium hydrogencarbonate solution was added to neutralize the reaction solution, followed by extraction with dichloromethane (60 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-100%) to afford the desired product (46 mg, yield 54%) as a pale yellow solid.

Provenance & Evidence