反应详情

Example 4 (25 mg, 0.051 mmol), TMS-acetylene (6 mg, 0.051 mmol), copper iodide (1 mg, 0.0005 mmol), triethylamine (1.0 mL, 0.014 mmol), and dichlorobis(triphenylphosphine)palladium(II) (1 mg, 0.0005 mmol) were stirred in 1:1 THF/DMF (2 mL) at room temperature for 3 h. The solution was concentrated in vacuo and purified by silica gel chromatography (10% MeOH/CH2Cl2) to give a tan oil. The intermediate was dissolved in 1:1 THF/MeOH (2 mL) and solid potassium carbonate (14 mg, 0.10 mmol) was added and the mixture stirred for 1 hr. The potassium carbonate was filtered off and the solution was concentrated in vacuo and purified by prep HPLC (25/50, water/acetonitrile) to give 12 mg (60%) of the title compound as a white solid. 1H NMR (400 MHz, MeOD-d4): δ 7.15-7.27 (m, 2H), 7.00 (t, 1H, J=8.3 Hz), 4.16 (t, 1H, J=7.3 Hz), 3.83-3.84 (m, 2H), 3.68-3.69 (m, 2H), 3.51 (s, 1H), 3.27 (t, 2H, J=7.6 Hz), 2.28 (s, 1H), 2.24 (m, 2H). MS (ES) [m+H] calc'd for C19H17F2N3O4, 390. found 390.

1. concentrationThe solution was concentrated in vacuo
2. custompurified by silica gel chromatography (10% MeOH/CH2Cl2)
3. customto give a tan oil
4. additionwas added
5. filtrationThe potassium carbonate was filtered off
6. concentrationthe solution was concentrated in vacuo
7. custompurified by prep HPLC (25/50, water/acetonitrile)