Potassium Carbonate → 4-(4-bromo-2,6-difluorophenyl)-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

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Reaction Conditions

Reaction Steps

To a round bottom flask, N-(4-bromo-2,6-difluorophenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide (2860 mg, 6.42 mmol) and potassium carbonate (4000 mg, 28.9 mmol) were added and suspended in water (200 mL). The mixture was refluxed for 16 h at 115° C. Analysis by LCMS indicated consumption of starting material and formation of desired product and by-products related to the starting material. The solution was neutralized to pH=7 with 1N aq HCl and 150 mL of ethyl acetate was added. The aqueous phase was extracted with ethyl acetate (3×) and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-20% isopropanol/ethyl acetate) provided the title product as a white solid (360 mg, 13%). MS(ES)+ m/e 426.9, 428.6 [M+H]+.

Provenance & Evidence