반응 #441261

반응 방정식

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

용매

THF

THF

THF

반응 조건

후처리

1. 1
   온도warmed 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
   기타The THF was removed
5. 5
   workup.ADDITIONthe residue diluted in water
6. 6
   추출extracted three times with Ethyl acetate
7. 7
   건조The combined organics were dried over anhydrous sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The crude material was chromatographed on silica gel using 1:20 THF/Hexanes to 1:10 THF/Hexanes as the gradient eluant

실험 절차

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.

출처