Dimethylformamide → HCID 86659961, compound

Participants

Reaction Conditions

Reaction Steps

In a 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser, 10b (500 mg, 1.52 mmol), 5-tert-Butyl-N-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carboxamide (600 mg, 1.50 mmol) and sodium carbonate (320 mg, 3.01 mmol) were mixed with DMF (8 mL), dioxane (5 mL) and water (2 mL). This mixture was degassed with nitrogen for 30 min. Tetrakis(triphenylphosphine)palladium (175 mg, 0.151 mmol) was added and the mixture was refluxed at 125° C. (bath temperature) for 14 h. The reaction mixture was then cooled to room temperature, and water (100 mL) was added. The resulting precipitate was filtered, and the filter cake was washed with water (250 mL). The filter cake was purified using a silica gel column eluting the desired product with 4-6% methanol in methylene chloride to afford a 36% yield (310 mg) of 10d as a off-white solid: mp 120-121° C.; 1H NMR (500 MHz, CDCl3) δ 10.13 (s, 1H), 10.02 (s, 1H), 9.39 (s, 1H), 8.99 (d, 1H, J=7.5 Hz), 8.68 (s, 1H), 7.56 (br s, 1H), 7.22 (m, 1H), 6.88 (s, 1H), 5.15 (s, 1H), 3.85 (s, 1H), 3.64 (m, 1H), 3.50 (m, 3H), 1.92-1.82 (m, 3H, 1.71 (m, 1H), 1.42 (br s, 1811); MS (APCI+) m/z 566.9 (M+H).

Provenance & Evidence