反应详情

3-Bromomethyl-5-nitro-indazole-1-carboxylic acid tert-butyl ester (0.63 g, 1.77 mmol) and potassium phthalimide (0.396 g, 1.2 eq) were stirred in DMF (1 mL) at 80° C. for two hours. TLC (20% EtOAc/hexane) showed starting material consumed and new products formed. After DMF was evaporated, a residue, 1.33 g, was obtained. The resulting residue was stirred in DCM and filtered. The filtration cake then washed with DCM followed by hexane. The evaporation of the filtrate gave 0.79 g of crude. Flash chromatograph (20-30% EtOAc/hexane) gave a mixture, two spots shown on TLC. During the sample preparation, solid precipitated and the solid was collected, 95 mg. MS showed de-Boc product, (M+H)+ at 323. An adequate amount of this mixture was treated with TFA in DCM for two hours. TLC showed one spot and MS gave (M+H)+ at 323. The remaining mixture was stirred in a mixture of TFA (6 mL) and DCM (10 mL) for two hours. Evaporation of TFA and DCM gave the desired product, 0.71 g, (quant. yield).

1. customconsumed
2. customnew products formed
3. customAfter DMF was evaporated
4. customa residue, 1.33 g, was obtained
5. filtrationfiltered
6. washThe filtration cake then washed with DCM
7. customThe evaporation of the filtrate
8. customgave 0.79 g of crude
9. customDuring the sample preparation, solid
10. customprecipitated
11. customthe solid was collected
12. additionAn adequate amount of this mixture was treated with TFA in DCM for two hours
13. customgave (M+H)+ at 323
14. customEvaporation of TFA and DCM