Reacción #554568

ord-48bd6ccb37be4985b64204451b59cf70

Ecuación de reacción

O
H2O
OB(O)c1cc2ccccc2s1
Benzo[b]thiophene-2-ylboronic acid
Clc1ccc2cnc3ccccc3c2c1
9-chlorophenanthridin
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
c1ccc2sc(-c3ccc4cnc5ccccc5c4c3)cc2c1
9-Benzothienylphenanthridine
Rendimiento 78.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaby refluxing under a N2 atmosphere for 5 hours
  2. 2
    Extracciónthe mixture was extracted with chloroform
  3. 3
    Secadoby drying with sodium sulfate
  4. 4
    FiltraciónAfter filtration
  5. 5
    Otrothe filtrate was evaporated to dryness under reduced pressure
  6. 6
    OtroThe obtained solid was purified by column chromatography (eluent: chloroform) (amount: 1.15 g, yield: 78%)

Procedimiento

Benzo[b]thiophene-2-ylboronic acid (884 mg, 5.0 mmol) and 9-chlorophenanthridin (1.0 g, 4.8 mmol) were dissolved in tetrahydrofuran (30 ml), and palladium catalyst (160 mg, 0.14 mmol) and 2M sodium carbonate solution (20 ml) were added, followed by refluxing under a N2 atmosphere for 5 hours. The reaction solution was added to H2O and the mixture was extracted with chloroform, followed by drying with sodium sulfate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The obtained solid was purified by column chromatography (eluent: chloroform) (amount: 1.15 g, yield: 78%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08623239B2uspto-grants-2014_01