6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene → (6-Chloro-pyridin-3-yl)-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophen-3-yl]-methanone

To a suspension of 2-Chloropyridine-5-carbonyl chloride (4.23 gm, 24 mmol) and 6-Methoxy-2-(4-methoxy-phenyl) -benzo[b]thiophene (5.0 gm, 18.5 mmol) in 275 mL of methylene chloride was added aluminum trichloride (18.59 g, 138.8 mmol) in three portions. The black-red reaction was stirred for 16 hrs. at room temperature. The reaction was then quenched with 400 mL of 2N NaOH (slowly and cooled in ice) and extracted into 300 mL of methylene chloride. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to a yellow solid which was chromatographed on silica gel using 5% to 20% Ethyl acetate/Hexanes as the gradient eluant to yield 2.47 gm of the title compound.

1. customThe black-red reaction
2. customat room temperature
3. customThe reaction was then quenched with 400 mL of 2N NaOH (slowly and
4. temperaturecooled in ice) and
5. extractionextracted into 300 mL of methylene chloride
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to a yellow solid which
10. customwas chromatographed on silica gel using 5% to 20% Ethyl acetate/Hexanes as the gradient eluant

ORD record

ord-7931cbc65c364b249cb01a240934fdec

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06756388B1