Hydrochloric Acid → HCID 86646394, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(5-bromo-2-methylthiophen-3-yl)-1,3-dioxolane (3.25 g) synthesized in Example 278 (3), 4-(trifluoromethyl)phenylboronic acid (3.70 g), sodium carbonate (2.76 g), water (10 mL) and N,N-dimethylformamide (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II).dichloromethane adduct (1.06 g). The reaction mixture was deaerated and stirred at 80° C. for 4 hr under an argon atmosphere. Phosphate buffer was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give a pale-yellow solid. To a solution of the obtained solid in tetrahydrofuran (25 mL) was added 1N hydrochloric acid (10 mL), and the mixture was stirred at room temperature for 1 hr. Tetrahydrofuran was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (2.33 g, 66%) as a white solid.

Provenance & Evidence