Triethylamine → 1-(cyclopropylmethyl)-5-(pyridin-3-ylethynyl)-4-(trifluoromethyl)-1H-benzotriazole

Participants

Reaction Conditions

Reaction Steps

1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl trifluoromethanesulfonate (25 mg, 0.064 mmol), 3-ethynylpyridine (13.3 mg, 0.128 mmol), triethylamine (116 μL, 0.835 mmol), tetra-n-butyl ammonium iodide (0.1 equiv), and copper (I) iodide (4 mg, 0.019 mmol) were combined in DMF (0.64 mL) and the mixture was sparged under nitrogen. Tetrakis(triphenylphosphine) palladium (0) (7.4 mg, 0.0064 mmol) was added, the mixture was sparged under nitrogen and then heated at 90° C. for 18 hours. The mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with water and brine. The organic extract was dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (0-55% EtOAc in hexanes), providing the titled compound as a light yellow solid: 1H-NMR (400 MHz, CDCl3) δ 8.82 (s, 1H), 8.61 (dd, J=4.9, 1.7 Hz, 1H), 7.87 (dt, J=7.9, 2.0 Hz, 1H), 7.76 (s, 2H), 7.34 (dd, J=7.9, 4.9 Hz, 1H), 4.58 (d, J=7.2 Hz, 2H), 1.41 (m, 1H), 0.66-0.73 (m, 2H), 0.51-0.55 (m, 2H) ppm; LRMS (ES+) m/z 343.1 [(M+H)+; calculated for C18H14F3N4: 343.2].

Provenance & Evidence