反应详情

Triphenylphosphine polymer bound (200 mg; 0.60 mmol; 0.15 eq.), palladium (II) acetate (60.17 mg; 0.27 mmol; 0.07 eq.) and DMF (12 mL) were first mixed in a microwave vial, purged with N2 and let stirring at RT for 2 h. The vial was then opened, zinc cyanide (469.70 mg; 4 mmol; 1 eq.) and methyl 5-bromo-2-fluorobenzoate, prepared from literature procedure starting from 5-bromo-2-fluorobenzoic acid (COMBI-BLOCKS; CA-4097) (932.15 mg; 4 mmol; 1 eq.), were added and the resulting mixture was purged once more and sealed. It was then heated in the microwave at 140° C. for 50 min. The reaction mixture was filtrated through a glass frit and the resin was washed with Et2O (3×10 mL). The combined organic solutions were washed with water (3×5 mL), once with NaCl sat. solution (10 mL) and then dried over magnesium sulfate. Evaporation of the solvents gave the title compound as a white solid (638 mg; 89%). 1H NMR (DMSO-d6, 300 MHz) δ 8.35 (dd, J=6.8, 2.2 Hz, 1H), 8.2-8.17 (m, 1H), 7.63 (dd, J=10.6. 8.6 Hz, 1H), 3.89 (s, 3H). GC/MS: 179. HPLC (Method A), Rt 2.74 min (purity: 93.9%).

1. additionwere first mixed in a microwave vial
2. custompurged with N2
3. additionwere added
4. customthe resulting mixture was purged once more
5. customsealed
6. temperatureIt was then heated in the microwave at 140° C. for 50 min
7. filtrationThe reaction mixture was filtrated through a glass frit
8. washthe resin was washed with Et2O (3×10 mL)
9. washThe combined organic solutions were washed with water (3×5 mL), once with NaCl sat. solution (10 mL)
10. dry with materialdried over magnesium sulfate
11. customEvaporation of the solvents