HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1023470Erstellt: 27. Oktober 2026
Dimethylformamide → 2-Chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridine
https://huagongshe.com/reaction/1023470
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Dimethylformamide | HCID 6228 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 2-Chloropyridine-4-boronic acid, pinacol ester | HCID 5103408 | — |
| Edukt | Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester | HCID 86673616 | — |
| Katalysator | HCID 178419050 | HCID 178419050 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Produkt | 2-Chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridine | HCID 86673617 | 58,3% |
Reaktionsschritte
Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester (200 mg, 0.62 mmol), 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (162 mg, 0.68 mmol), Bis(triphenylphosphine)Palladium (II) dichloride (43 mg, 0.062 mmol), Sodium Carbonate solution (2.0 M, 1.54 mL, 3.1 mmol) and DMF (3 mL) are mixed in a 5 mL microwave tube with a stir bar and the mixture is heated to 100° C. in microwave reactor for 30 min. The mixture is poured to water (10 mL) and extracted with EtOAc (10 mL×3). The organic extracts are washed with water (20 mL×1), brine (20 mL×1) and dried over anhydrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 20%) to give 104 mg of the desired product.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08722709B2 |
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| Quelldatensatz | uspto-grants-2014_05 |
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| ORD ID | ord-f918b3db77804691a76161ae6aea9624 |
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| Quellennotiz | uspto-grants-2014_05 |
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