2-Chloronicotinonitrile → HCID 22285317, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloronicotinonitrile (2.49 g, 18.02 mmol), 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (from Example 2, step d) (6.14 g, 23.43 mmol) and potassium fluoride (3.46 g, 59.47 mmol) in tetrahydrofuran (120 ml), was degassed with nitrogen for 30 min then treated with tris(dibenzylideneacetone)dipalladium(0) (0.33 g, 0.360 mmol), followed by tri-tert-butylphosphine (3.6 ml of a 0.2 M solution in 1,4-dioxane, 0.721 mmol). The mixture was degassed again before heating at 50° C. for 18 h. The mixture was cooled to ambient temperature then partitioned between ethyl acetate and water. The organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2) to afford 3.759 g (86%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 8.97 (1H, dd, J 5, 2 Hz), 8.56 (1H, dd, J 6, 3 Hz), 8.40-8.45 (1H, m), 8.15 (1H, dd, J 8, 2 Hz), 7.55 (1H, dd, J 8, 5 Hz), 7.43 (1H, dd, J 9, 9 Hz); MS (ES+) m/z 244 [M+H]+.

Provenance & Evidence