Sodium hydride → 5-(Azetidin-1-ylcarbonyl)-2-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylpyridine

Participants

Reaction Conditions

Reaction Steps

t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (59 mg, 0.137 mmol) synthesized in Example (38d) and 5-(azetidin-1-ylcarbonyl)-2-chloro-3-methylpyridine (45 mg, 0.232 mmol) synthesized in Example (61a) were dissolved in dimethyl sulfoxide (3.0 mL), and sodium hydride (60%, 25 mg, 0.63 mmol) was added, followed by stirring at 80° C. for 4.5 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with ethyl acetate (30 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=60%-80%) to afford the desired compound (50 mg, yield 72%) as a yellow solid.

Provenance & Evidence