Reacción #554566

ord-7c98e88a3df4448fa6806a86354cfdb8

Ecuación de reacción

O
H2O
OB(O)c1cc2ccccc2s1
Benzo[b]thiophene-2-ylboronic acid
Clc1nccc2ccccc12
1-chloroisoquinoline
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
c1ccc2sc(-c3nccc4ccccc34)cc2c1
1-Benzothienylisoquinoline
Rendimiento 79.0%

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: 1.16 g, yield: 79%)

Procedimiento

Benzo[b]thiophene-2-ylboronic acid (997 mg, 5.6 mmol) and 1-chloroisoquinoline (946 mg, 5.8 mmol) were dissolved in toluene (20 ml) and ethanol (10 ml), and palladium catalyst (220 mg, 0.19 mmol) and 2M sodium carbonate solution (20 ml) were added thereto, 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: 1.16 g, yield: 79%).

Fuente

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