Potassium Phosphate, Tribasic → HCID 70978021, compound

Participants

Reaction Steps

4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl trifluoromethanesulfonate (0.22 g, 0.62 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-ene-1-carboxylate (0.21 g, 0.77 mmol, 1.25 equiv), potassium phosphate (0.39 g, 1.8 mmol, 3 equiv) and tetrakis(triphenylphosphine)palladium(0) (71 mg, 0.062 mmol, 0.1 equiv) were combined in a degassed mixture of dioxane (5 mL) and water (0.5 mL) and placed into a preheated oil bath at 90° C. for 90 minutes. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (75 mL, aqueous saturated) and extracted with ethyl acetate (2×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 25:75; hexanes:ethyl acetate), providing the titled compound as a colorless oil: 1H-NMR (400 MHz, d6-DMSO) δ 7.88 (1H, d, J=8.5 Hz), 7.41 (1H, d, J=8.5 Hz), 5.77-5.74 (1H, m), 4.61 (2H, d, J=7.7 Hz), 3.66 (3H, s), 3.37-3.32 (2H, m), 2.75-2.69 (1H, m), 2.49-2.30 (2H, m), 2.11-2.05 (1H, m), 1.84-1.76 (1H, m), 1.41-1.33 (1H, m), 0.57-0.53 (2H, m), 0.49-0.45 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 346.1316 [(M+H)+; calculated for C18H21ClN3O2: 346.1317].

Provenance & Evidence