HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 422103Erstellt: 24. Oktober 2026
Dichloromethane → 4-Benzo[b]thiophen-7-yl-2-fluoro-5-methyl-pyridine
https://huagongshe.com/de/reaction/422103
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 2-Fluoro-4-iodo-5-methylpyridine | HCID 10060052 | — |
| Edukt | 2-(Benzo[b]thiophen-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 66673976 | — |
| 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-fluoro-5-methyl-pyridine | HCID 66674047 | 82,2% |
Reaktionsschritte
In a flask, combine 2-fluoro-4-iodo-5-methyl-pyridine (355 mg, 1.5 mmol), 2-benzo[b]thiophen-7-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (282 mg, 1.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (61 mg, 0.07 mmol), 2-(di-tert-butylphosphino)biphenyl (13 mg, 0.04 mmol), sodium carbonate (2 M, 1.5 mL, 3 mmol) and THF (10 mL). Heat the mixture at 100° C. for 3 hours in an oil bath. Dilute the mixture with chloroform/isopropanol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate in vacuo to a dark residue. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound (300 mg, 82%) as yellow oil. MS (ES) m/z 244 [M+1]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08101628B2 |
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| Quelldatensatz | uspto-grants-2012_01 |
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| ORD ID | ord-67153add23f04a72b4d18cb246fd63c5 |
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| Quellennotiz | uspto-grants-2012_01 |
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