反应详情

A mixture of compound 18a (0.74 g, 2.4 mmol) and 2-bromoquinoline (2.0 g, 9.6 mmol) in a vial was evacuated and back-flushed with Argon. Dry DMF (10 mL) and DIEA (1.7 mL, 9.7 mmol) were added via syringe and the mixture was deoxygenated by bubbling Argon through the stirred solution for 5 min. To the mixture was added CuI (46 mg, 0.24 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.17 g, 0.24 mmol). The reaction mixture was stirred at rt overnight, and was poured into water (50 mL). The mixture was extracted with EtOAc (3×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), and dried over Na2SO4. The mixture was filtered, and the filtrate was concentrated to obtain a residue which was purified by flash column chromatography on silica gel (30-70% EtOAc/heptane) to obtain compound 18b as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H16BrN5O: 434.1 (M+H). found: 434.2.

1. customwas evacuated
2. customback-flushed with Argon
3. customthe mixture was deoxygenated
4. customby bubbling Argon through the stirred solution for 5 min
5. extractionThe mixture was extracted with EtOAc (3×30 mL)
6. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
7. dry with materialdried over Na2SO4
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated
10. customto obtain a residue which
11. customwas purified by flash column chromatography on silica gel (30-70% EtOAc/heptane)