Diisopropylethylamine → 7-Fluoro-2-[3-(hydroxymethyl)azetidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

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Reaction Steps

Under nitrogen atmosphere, 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (240 mg, 0.84 mmol) was dissolved in methylene chloride (10 ml), then diisopropylethylamine (584 μl, 3.35 mmol) and 3-hydroxymethylazetidine (206 mg, 1.67 mmol) dissolved in methylene chloride (5 ml) were added, followed by heating under reflux in a sealed tube for 5 hours. After cooling, diluting with chloroform and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (208 mg, 74%) as a white solid.

Provenance & Evidence