Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Iodine | HCID 807 | — |
| Edukt | Potassium Hydroxide | HCID 14797 | — |
| Edukt | tert-Butyl 4-(1H-indazol-4-yl)piperazine-1-carboxylate | HCID 44242883 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 178452228 | HCID 178452228 | 35% |
Reaktionsschritte
A solution of 4-[4-(t-butoxycarbonyl)piperazin-1-yl]-1H-indazole (5.00 g, 16.5 mmol) in N,N-dimethylformamide is treated with powdered potassium hydroxide (1.85 g, 33.07 mmol) and iodine (4.61 g, 18.2 mmol), stirred at room temperature for 16 h, diluted with ethyl acetate and quenched with 15% aqueous sodium metabisulfite. The phases are separated and the aqueous phase is extracted with ethyl acetate. The extracts and the organic phase are combined, washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a crude solid. This solid is purified by column chromatography (silica gel, 10:90 to 15:85 to 20:80 ethyl acetate/hexanes) to afford the title product as a yellow solid, 2.40 g (35% yield) identified by HNMR and mass spectral analyses.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07238696B2 |
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| Quelldatensatz | uspto-grants-2007_07 |
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| ORD ID | ord-226209d34af24dffb58a30d75843ff2b |
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| Quellennotiz | uspto-grants-2007_07 |
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