Reacción #441261

Ecuación de reacción

n-BuLi

product

Trifluoro-methanesulfonic acid benzothiazol-6-yl ester

lithium chloride

6-methoxybenzo[b]thiophene

→

title compound

6-(6-Methoxy-benzo[b]thiophen-2-yl)-benzothiazole

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawarmed to room temperature for an additional 0.5 hrs
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature for 15 minutes
3. 3
   workup.STIRRINGThe reaction was stirred at room temperature for 16 hrs
4. 4
   OtroThe THF was removed
5. 5
   workup.ADDITIONthe residue diluted in water
6. 6
   Extracciónextracted three times with Ethyl acetate
7. 7
   SecadoThe combined organics were dried over anhydrous sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated
10. 10
    OtroThe crude material was chromatographed on silica gel using 1:20 THF/Hexanes to 1:10 THF/Hexanes as the gradient eluant

Procedimiento

A solution of 6-methoxybenzo[b]thiophene (300 mg, 1.82 mmol) in 5 mL of THF was cooled to −20° C. and 2.5 M n-BuLi (0.8 mL, 2.01 mmol) was added dropwise. The reaction was stirred at 0° C. for 0.5 hrs and then warmed to room temperature for an additional 0.5 hrs. Next a 0.5 M solution of anhydrous zinc chloride in THF (4.75 mL, 2.38 mmol) was added and the reaction was stirred at room temperature for 15 minutes followed by the addition of anhydrous lithium chloride (3 equivalents), tetrakis-triphenylphosphine palladium (84 mg, 0.073 mmol) and, by cannula, the product from Example 18, Step 1 (505 mg, 2.01 mmol) dissolved in 2 mL of THF. The reaction was stirred at room temperature for 16 hrs. The THF was removed and the residue diluted in water and extracted three times with Ethyl acetate. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was chromatographed on silica gel using 1:20 THF/Hexanes to 1:10 THF/Hexanes as the gradient eluant to yield the title compound.

Fuente