Dimethylformamide → HCID 89442827, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1.0 g, 1.77 mmol, Intermediate 1), 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropane carbaldehyde (762.0 mg, 2.80 mmol), Pd(dppf)Cl2 (76 mg, 0.09 mmol) and sodium carbonate (591.0 mg, 5.58 mmol) under nitrogen atmosphere, was added DMF and H2O (9 mL, 1:1). The reaction mixture was heated at 80° C. for 1 h. After the completion of the reaction as confirmed by TLC, the solution was cooled to r.t and filtered through celite. The solvent was concentrated in vacuo. The crude compound was diluted with ethyl acetate (100 mL). The organic layer was washed with water (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (silica gel, 1:4 EtOAc:Pet ether) to afford the title compound (320 mg, 29%) as a white solid

Provenance & Evidence