Bromoacetonitrile → HCID 17895494, compound

Participants

Reaction Steps

To a stirred solution of 3,7-diphenyl-1,2,4-triazolo[4,3-b]pyridazin-6-one (from Example 73, Step a) (0.4021 g, 1.39 mmol) in anhydrous DMF (20 ml) under nitrogen was added sodium hydride (60% dispersion in oil, 84.0 mg, 2.10 mmol) and the mixture was stirred at room temperature for 30 min,. then at 80° C. for 20 min. After allowing to cool, bromoacetonitrile (0.146 ml, 2.10 mmol) was added dropwise and the mixture was stirred at room temperature for 14 h. The mixture was then partitioned between ethyl acetate (100 ml) and water (100 ml), adding saturated aqueous NaCl to aid in the separation of the layers. The aqueous layer was extracted further with ethyl acetate (2×100 ml) and the combined organic extracts were dried (Na2SO4), and evaporated in vacua. The residue was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2) to afford 0.4566 g (100%) of the title compound as a buff solid: 1H NMR (360 MHz, CDCl3) δ5.11 (2 H, s), 7.52-7.63 (8 H, m), 8.12 (1 H, s), 8.45 (2 H, m); MS (ES+) m/e 328 [MH]+.

Provenance & Evidence