反应详情

A mixture of 5.8 g (17 mmol) of 3-iodo-2-methyl-4-methylsulfonylbenzoic acid, 4.0 g (23.8 mmol) of 4-methylthiophenylboronic acid, 11.7 g (85 mmol) of potassium carbonate, 50 mL of acetonitrile, and 12 mL of water was prepared and purged with nitrogen gas with stirring. The catalyst system, 190 mg (0.85 mmol) of palladium II acetate and 775 g (2.25 mmol) of tri-o-tolylphosphine, was added and the mixture was heated to reflux with stirring for several hours. The mixture was then cooled, basified with dilute aqueous sodium hydroxide solution, extracted with ether, and then acidified with concentrated aqueous hydrochloric acid. The resulting mixture was extracted with ether and the extract was concentrated by evaporation under reduced pressure. The residue was diluted with ethyl acetate and again concentrated by evaporation under reduced pressure. The residue was chromatographed on a preparative C-18 high pressure liquid chromatography (HPLC) column eluting with a 60:40:0.05 mixture of acetonitrile, water, and acetic acid. The product fractions were combined and extracted with ether. The ethereal extracts were concentrated by evaporation under reduced pressure and the residue obtained was diluted with ethyl acetate and again concentrated by evaporation under reduced pressure. The residue obtained was mixed with hexane and the insoluble solids were recovered by filtration and dried to obtain 2.2 g (39 percent of theory) of the title compound as a tan powder melting at 178-179° C.

1. customwas prepared
2. custompurged with nitrogen gas
3. temperaturethe mixture was heated
4. temperatureto reflux
5. stirringwith stirring for several hours
6. temperatureThe mixture was then cooled
7. extractionextracted with ether
8. extractionThe resulting mixture was extracted with ether
9. concentrationthe extract was concentrated by evaporation under reduced pressure
10. additionThe residue was diluted with ethyl acetate
11. concentrationagain concentrated by evaporation under reduced pressure
12. customThe residue was chromatographed on a preparative C-18 high pressure liquid chromatography (HPLC) column
13. washeluting with a 60:40:0.05 mixture of acetonitrile, water, and acetic acid
14. extractionextracted with ether
15. concentrationThe ethereal extracts were concentrated by evaporation under reduced pressure
16. customthe residue obtained
17. concentrationagain concentrated by evaporation under reduced pressure
18. customThe residue obtained
19. filtrationthe insoluble solids were recovered by filtration
20. customdried