Diisopropylethylamine → HCID 22592273, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-propyn-3-yl-1H-[1,2,3]triazol (0.086 g, 0.8 mmol) in N,N-dimethylformamide (“DMF”, 1 mL) was treated with the N-(4-cyano-benzyl)-3-iodo-benzamide (0.225 g, 0.62 mmol) prepared in Step (1), diisopropylethylamine (0.32 g, 2.5 mmol), copper (I) iodide (0.024 g, 0.013 mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.025 g, 0.004 mmol), respectively. The reaction mixture was stirred under nitrogen atmosphere for 5 hours at 55° C., then cooled to room temperature. The crude reaction mixture was diluted with THF (5 mL) and passed through a pad of silica gel (elution with THF). The partially purified product obtained was further purified using silica gel chromatography (elution with THF/hexane [3:1]) to give the title compound (0.077 g, 36%) as cream color solid. 1H-NMR (CDCl3/DMSO-d6) δ 8.3 (m, 1H), 7.9 (s, 1H), 7.8 (m, 2H), 7.6 (s, 1H), 7.4 (m, 3H), 7.3 (m, 2H), 5.3 (s, 2H), 4.5 (d, 2H) ppm. Mp 145° C.-147° C.

Provenance & Evidence