Boron tribromide → HCID 135977437, compound

Participants

Reaction Steps

2-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-5-(methylsulfonyl)pyrazine (382 mg, 0.79 mmol) synthesized in Example (970 was dissolved in methylene chloride (10 mL), and boron tribromide (1.0 mol/L methylene chloride solution, 1.58 mL, 1.58 mmol) was added at −78° C. under nitrogen atmosphere. Subsequently the temperature was brought back to room temperature, followed by stirring for 1.5 hours under nitrogen atmosphere. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=0%-5%) to afford the desired compound (219 mg, yield 59%) as a white solid.

Provenance & Evidence