Nitrogen → (E)-Ethyl 3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazol-5-yl)but-1-en-1-yl)phenyl)acrylate

Participants

Reaction Conditions

Reaction Steps

A 100-mL round-bottom flask equipped with a magnetic stir bar, a rubber septum and N2 inlet was charged with 5-(but-1-yn-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazole (0.2 g, 0.78 mmol), iodobenzene (0.48 g, 2.35 mmol), (E)-(4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)boronic acid (0.51 g, 2.35 mmol), K2CO3 (0.32 g, 2.35 mmol), and N,N-dimethylformamide/water (2:1, 39 mL). This mixture was degassed with three vacuum/N2 cycles and then heated at 45° C. for 10 minutes. With continued heating, a solution of Pd(PhCN)2Cl2 (0.003 g, 0.008 mmol) in N,N-dimethylformamide (0.2 mL) was added dropwise. The resulting mixture was stirred at 45° C. overnight. The reaction was monitored by TLC. Upon completion, the reaction mixture was cooled down to room temperature, quenched with water (100 mL), and extracted with ethyl acetate (2×200 mL). The combined organics were washed with water (100 mL), washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated to give the crude product. This crude material was purified on a silica gel column eluted with 0-25% ethyl acetate in hexanes affording the title compound as an off-white solid (0.28 g). LCMS: 424 [(M-THP+H)+H]+.

Provenance & Evidence