Ethyl Acetate → HCID 22390221, compound

Participants

Reaction Conditions

Reaction Steps

A ketone compound (1.96 g) was prepared in substantially the same manner as in step b) of Synthesis Example 1, except that 2.77 g of 7-[(5-bromopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole and 2.00 g of manganese dioxide were used as the starting compounds. The ketone compound (616 mg) was dissolved in 20 ml of N,N-dimethylformamide to prepare a solution. Diethyl(3-pyridyl)borane (588 mg), 232 mg of tetrakis(triphenylphosphine)palladium(0), and 552 mg of potassium carbonate were added to the solution at room temperature under an argon atmosphere. The mixture was stirred at 90° C. for 2.5 hr. Ethyl acetate (200 ml) was added to the reaction solution, and the organic layer was washed four times with 80 ml of water and once with saturated brine. The washed organic layer was dried over anhydrous magnesium sulfate and was filtered. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel (chloroform/methanol=20/1 →10/1) to give 428 mg of 7-([3,3′]bipyridinyl-5-yl)carbonylimidazo[5,1-b]thiazole.

Provenance & Evidence