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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 501049Erstellt: 24. Oktober 2026

Benzo(B)Thiophene-2-Boronic Acid → 5-(1-Benzothien-2-yl)pyridine-2-carboxamide

https://huagongshe.com/de/reaction/501049

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktBenzo(B)Thiophene-2-Boronic AcidHCID 2359—
EduktPotassium CarbonateHCID 11430—
Edukt5-Bromopyridine-2-carboxamideHCID 735151—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
LösungsmittelDimethylformamideHCID 6228—
Produkt5-(1-Benzothien-2-yl)pyridine-2-carboxamideHCID 250149303,6%

Reaktionsschritte

2-Benzothienylboronic acid (1.8 mmol), 5-bromopyridine-2-carboxamide (1.2 mmol), 2M K2CO3 (2.4 mL), Pd(dppf)Cl2 (0.12 mmol) were mixed and stirred at 80° C. in DMF for 3 h. The reaction mixture was filtered and to the filtrated was added EtOAc and H2O. The layers were separated and the aqueous phase was extracted twice with EtOAc. The organic extracts were dried over Na2SO4. The solvent was evaporated in vacuo to give a brown solid. The crude was subjected to reverse phase HPLC to afford the title compound as a light brown solid (11 mg). 1H NMR δ ppm 9.07 (d, 1 H) 8.34 (dd, 1 H) 8.24-8.02 (m, 5 H) 7.73 (s br, 1 H) 7.54-7.37 (m, 2 H); MS m/z 255 (M+H).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07772256B2
Quelldatensatzuspto-grants-2010_08
ORD IDord-a032e3afb19e418595dd11b2e977e424
Quellennotizuspto-grants-2010_08