Reaction #554566

Reaction equation

H2O

Benzo[b]thiophene-2-ylboronic acid

1-chloroisoquinoline

sodium carbonate

→

1-Benzothienylisoquinoline

Yield 79.0%

Solvents

toluene

ethanol

Conditions

Workup

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

Procedure

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