Ethanol → HCID 71185764, compound

Temperature

97.5 °C

(4-methoxyphenyl)boronic acid (0.56 g, 3.70 mmol) and potassium carbonate (1.40 g, 10.11 mmol) were added to a solution of methyl 5-bromo-3,4-dimethylthiophene-2-carboxylate (9b, 0.8 g, 3.37 mmol) in a mixture of toluene:ethanol (10:30 ml) in a tube at 25° C. Nitrogen gas was bubbled through reaction mixture for 15 minutes. Tetrakis(triphenylphosphine)(0)palladium (0.19 g, 0.17 mmol) was added to the reaction mixture under nitrogen and the tube was sealed. The reaction mixture was heated at 95-100° C. for 2 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and was filtered through celite. The celite cake was washed with ethyl acetate (30 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was further purified by column chromatography using 5% ethyl acetate in hexanes as an eluent to obtain the title compound 9c (0.84 g, 90%).

1. customat 25° C
2. customNitrogen gas was bubbled through reaction mixture for 15 minutes
3. customthe tube was sealed
4. temperatureThe reaction mixture was then cooled to 25° C.
5. filtrationwas filtered through celite
6. washThe celite cake was washed with ethyl acetate (30 ml)
7. concentrationThe combined filtrate was concentrated under reduced pressure
8. customto obtain a crude product
9. customThe resulting crude product was further purified by column chromatography

ORD record

ord-e3eb6b3b866a415bb88a77128f129ea0

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946432B2