Réaction #554566

ord-7c98e88a3df4448fa6806a86354cfdb8

Équation de réaction

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
Rendement 79.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureby refluxing under a N2 atmosphere for 5 hours
  2. 2
    Extractionthe mixture was extracted with chloroform
  3. 3
    Séchageby drying with sodium sulfate
  4. 4
    FiltrationAfter filtration
  5. 5
    Autrethe filtrate was evaporated to dryness under reduced pressure
  6. 6
    AutreThe obtained solid was purified by column chromatography (eluent: chloroform) (amount: 1.16 g, yield: 79%)

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08623239B2uspto-grants-2014_01