4-Fluoroiodobenzene → HCID 86706519, compound

Participants

Reaction Conditions

Reaction Steps

Copper (I) iodide (0.02 g, 0.1 mmol) was added to a stirred suspension of 2-(benzyloxy)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (0.5 g, 1.94 mmol), 4-iodofluorobenzene (0.63 g, 2.8 mmol) and N,N-dimethylethylenediamine (0.034 g, 0.38 mmol) in 1,4-dioxane (20 mL). The reaction mixture was stirred at 110° C. for 16 hours and then the solvent was evaporated in vacuo. The mixture was diluted with water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by preparative-HPLC (Gemini 250 Å×20 mm, gradient ACN in water from 41% to 71% with 0.05% NH4OH in water) to yield 2-(benzyloxy)-5-(4-fluorophenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (0.42 g, 62% yield). C20H18FN3O2. 1H NMR (400 MHz, CDCl3) δ ppm 2.35 (quin, J=6.6 Hz, 2H), 3.80 (t, J=6.3 Hz, 2H), 4.43 (t, J=6.9 Hz, 2H), 5.20 (s, 2H), 6.27 (s, 1H), 7.07-7.17 (m, 2H), 7.27-7.42 (m, 5H), 7.42-7.48 (m, 2H).

Provenance & Evidence