Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Edukt | (Diethylamino)(difluoro)sulfanium tetrafluoroborate | HCID 44517918 | — |
| Edukt | HCID 66793408 | HCID 66793408 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 66793261 | HCID 66793261 | 9,9% |
Reaktionsschritte
To a solution of 4-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-3-yn-1-ol (1.0 g, 3.7 mmol; Intermediate 20) in dry dichloromethane (25 mL), was added triethylamine.3HF (1.2 g, 7.4 mmol). XtalFluor-E (1.2 g, 5.5 mmol) was then added. The resulting solution was stirred at room temperature for 30 minutes. Upon completion, the reaction solution was neutralized by slow addition of saturated NaHCO3 (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0-20% EtOAc in petroleum ether) affording the title compound (100 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.88 (s, 1H), 7.73 (d, 1H), 7.42 (dd, 1H), 5.86 (dd, 1H), 4.60 (dt, 2H), 3.88 (m, 1H), 3.78-3.71 (m, 1H), 2.89 (dt, 2H), 2.48-2.34 (m, 1H), 2.06-1.95 (m, 2H), 1.78-1.72 (m, 1H), 1.58 (m, 2H); LCMS: 273 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09399646B2 |
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| Quelldatensatz | uspto-grants-2016_07 |
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| ORD ID | ord-6b800577c28c4f94aef6de77c3ba0525 |
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| Quellennotiz | uspto-grants-2016_07 |
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