Sodium hydride → 5-butyl-4-[4-[(1-carbomethoxy)(1-phenyl)methoxy]phenyl]methyl-2-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

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Reaction Steps

A mixture of 64 mg (0.254 mmol) of the product of Step C, 6.1 mg (0.254 mmol) of sodium hydride, and 0.5 mL of DMF was stirred under N2 at room temperature for 2.5 hours. To this was then added 100 mg (0.299 mmol) of methyl 2-(4-bromomethylphenoxy)-2-phenylacetate (from Example 1, Step C), dissolved in a minimal amount of DMF. Stirring was continued for 48 hours. The mixture was then partitioned between 5 mL H2O and 8 mL EtOAc, and the aqueous layer was further extracted with 2×8 mL EtOAc. The combined organic layers were washed with 2×10 mL H2O and 1×10 mL brine, and dried over anhydrous Na2SO4. The filtrate was evaporated in vacuo, and the residue flash chromatographed over 40 mL silica gel (gradient elution with 0.5% to 2.0% methanol in CH2Cl2) to give 62 mg of the title compound as a colorless oil (48%), homogeneous by TLC in 50:1 CH2Cl2 --MeOH.

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