Reaktion #554566

ord-7c98e88a3df4448fa6806a86354cfdb8

Reaktionsgleichung

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
Ausbeute 79.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08623239B2uspto-grants-2014_01