Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 2-Chloropyridine-4-boronic acid, pinacol ester | HCID 5103408 | — |
| Edukt | 7-Bromobenzo[b]thiophene | HCID 12045538 | — |
| Katalysator | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Katalysator | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Lösungsmittel | Chloroform isopropyl alcohol | HCID 21906603 | — |
| Produkt | 4-Benzo[b]thiophen-7-yl-2-chloro-pyridine | HCID 86640254 | 66,3% |
Reaktionsschritte
In a flask, combine 7-bromo-benzo[b]thiophene (1.7 g, 12 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.6 g, 7 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (285 mg, 0.3 mmol), 2-(di-tert-butylphosphino)biphenyl (63 mg, 0.2 mmol), sodium carbonate (2 M, 8 mL, 16 mmol) and THF (20 mL). Heat the mixture at 100° C. for 3 hours. Dilute the mixture with chloroform/isopropanol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (dichloromethane to 20% THF in dichloromethane) to afford the title compound (1.14 g, 66%) as a yellow solid. MS (ES) m/z 246 [M+1]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08101628B2 |
|---|
| Quelldatensatz | uspto-grants-2012_01 |
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| ORD ID | ord-50a336f664f14e72bf0fed21c70efb66 |
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| Quellennotiz | uspto-grants-2012_01 |
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