反应详情

温度

100 °C

To a mixture of 7-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-22, 168 g, 0.55 mmol) and (rac)-N-[1-(5-bromo-pyridin-3-yl)-ethyl]-propionamide (125 mg, 0.5 mmol) in DMF (3 mL), purged with argon for 1 min, was added bis(triphenylphosphine)palladium(II)chloride (38 mg, 0.054 mmol) and 1 N aq. Na2CO3 (2.5 mL). Then, the resulting reaction mixture was heated in a microwave at 100° C. for 45 min. After cooling to room temperature, it was diluted with EtOAc (5 mL), and poured into satd. aq. solution of NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (3×5 mL) and combined organics were washed with water and brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was the purified by prep-HPLC to give the title compound (35 mg, 20%) as a white solid. MS: 356.3 (M+H+)+.

1. custompurged with argon for 1 min
2. customThen, the resulting reaction mixture
3. temperatureAfter cooling to room temperature
4. additionpoured into satd
5. extractionThe aqueous layer was extracted with EtOAc (3×5 mL)
6. washcombined organics were washed with water and brine (20 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. custompurified by prep-HPLC