1,4-Dioxane → HCID 72714885, compound

Participants

Reaction Conditions

Reaction Steps

Copper (I) iodide (0.011 g, 0.057 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 (0.3 g, 1.16 mmol), 2-bromo-6-fluoropyridine (0.25 g, 1.42 mmol), N,N-dimethylethylenediamine (0.02 g, 0.23 mmol) and K3PO4 (0.5 g, 2.36 mmol) in 1,4-dioxane (15 mL). The reaction mixture was stirred at 80° C. for 16 hours and then the solvent was evaporated in vacuo. The mixture was diluted with water and extracted with DCM. 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 40% to 70% with 0.05% NH4OH in water) to yield 2-(benzyloxy)-5-(5-fluoropyridin-2-yl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (0.151 g, 37% yield). C19H12FN4O2. 1H NMR (400 MHz, CDCl3) δ ppm 2.40 (quin, J=6.7 Hz, 2H), 4.18 (t, J=6.3 Hz, 2H), 4.35 (t, J=6.9 Hz, 2H), 5.21 (s, 2H), 6.28 (s, 1H), 7.30-7.42 (m, 3H), 7.43-7.50 (m, 3H), 8.12 (dd, J=9.3, 4.0 Hz, 1H), 8.26 (d, J=3.0 Hz, 1H).

Provenance & Evidence