反应详情

Cool a solution of 5-(tert-butyldimethylsilyloxy)-1H-indazole (300.00 g, 1.21 mol) in DCM (4.00 L) to 10° C. in a 10 L jacketed reactor vessel. To the resulting solution add N-iodosuccinimide (298.89 g, 1.33 mol) in portions over 0.5 hours. Stir the mixture at RT for 3 hours to give complete conversion as indicated by liquid chromatography mass spectrometry (LC-MS) and thin layer chromatography (TLC). Cool the mixture to 10° C. and quench with water (2.5 L). Transfer the mixture to a separatory funnel and extract the aqueous layer into DCM (2.5 L). Wash the combined organic extracts with a 10% aqueous sodium thiosulfate solution (5 L) and brine. Dry the organic solution over magnesium sulfate, filter and concentrate in vacuo to afford the title compound as an orange solid. Yield: 388 g (90%). MS (ES) m/z 375 [M+1]+.

1. customto give complete conversion
2. temperatureCool the mixture to 10° C.
3. customquench with water (2.5 L)
4. extractionTransfer the mixture to a separatory funnel and extract the aqueous layer into DCM (2.5 L)
5. washWash the combined organic extracts with a 10% aqueous sodium thiosulfate solution (5 L) and brine
6. dry with materialDry the organic solution over magnesium sulfate
7. filtrationfilter
8. concentrationconcentrate in vacuo