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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

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDichloromethaneHCID 6344—
EduktSodium CarbonateHCID 10340—
Edukt2-Fluoro-4-iodo-5-methylpyridineHCID 10060052—
Edukt2-(Benzo[b]thiophen-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66673976—
Katalysator2-(Di-tert-butylphosphino)biphenylHCID 2734215—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
LösungsmittelTetrahydrofuranHCID 8028—
LösungsmittelChloroform isopropyl alcoholHCID 21906603—
Produkt4-Benzo[b]thiophen-7-yl-2-fluoro-5-methyl-pyridineHCID 6667404782,2%

Reaktionsbedingungen

Temperatur100 °C

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08101628B2
Quelldatensatzuspto-grants-2012_01
ORD IDord-67153add23f04a72b4d18cb246fd63c5
Quellennotizuspto-grants-2012_01