Lithium Chloride → HCID 12992515, compound

Temperature

0 °C

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.

1. temperaturewarmed to room temperature for an additional 0.5 hrs
2. stirringthe reaction was stirred at room temperature for 15 minutes
3. stirringThe reaction was stirred at room temperature for 16 hrs
4. customThe THF was removed
5. additionthe residue diluted in water
6. extractionextracted three times with Ethyl acetate
7. dry with materialThe combined organics were dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude material was chromatographed on silica gel using 1:20 THF/Hexanes to 1:10 THF/Hexanes as the gradient eluant

ORD record

ord-ce06b0776db14cef985096f19f983d58

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06756388B1