反应详情

To a mixture of 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3 yl)oxy)piperidine-1-carbonitrile (intermediate-36) (0.110 g, 0.27 mmol) and N-hydroxy-isobutyramidine (0.05 g, 0.5 mmol) in anhydrous THF (15 mL), 1M solution of zinc chloride in THF (0.56 mL, 0.56 mmol) was added. The suspension was stirred at room temperature for 18 h. Solvent was concentrated in vacuo, the resulting crude was dissolved in 4N HCl in ethanol, water (1:1) and stirred at 60-70° C. for 2-3 h. The reaction was quenched by saturated NaHCO3 and the organic layer was separated and concentrated. The residue was purified by flash column chromatography to give 3-isopropyl-5-(4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidin-1-yl)-1,2,4-oxadiazole (0.041 g, 30%)

1. additionwas added
2. concentrationSolvent was concentrated in vacuo
3. dissolutionthe resulting crude was dissolved in 4N HCl in ethanol
4. stirringwater (1:1) and stirred at 60-70° C. for 2-3 h
5. customThe reaction was quenched by saturated NaHCO3
6. customthe organic layer was separated
7. concentrationconcentrated
8. customThe residue was purified by flash column chromatography