反应详情

(Some starting materials may be obtained from ECA International, Palatine, Ill.) To a microwave vial (5 mL), 2-chloro-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (0.110 g, 0.390 mmol), 6-bromo-4-chloroquinoline (0.102 g, 0.419 mmol), PdCl2 (dppf)-CH2Cl2 adduct (0.0183 g, 0.0224 mmol) and potassium carbonate (0.500 mL, 1.00 mmol) were added into 1,4-dioxane (3 mL). The mixture was degassed by bubbling nitrogen through for 10 min. The tube was irradiated with microwave at 100° C. for 10 min. The reaction was cooled to RT then partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (eluent: acetone in hexanes 0% -30%) to afford the title compound as a white solid (0.0884 g). m/z: calc'd for C16H13Cl2N3; 317.0, found: 318.1 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.97 (s, 6 H), 7.55-7.63 (m, 2 H), 7.98 (dd, J=8.8, 2.0 Hz, 1 H), 8.25 (d, J=8.8 Hz, 1 H), 8.38 (dd, J=5.3, 2.0 Hz, 2 H), 8.84 (d, J=4.7 Hz, 1 H).

1. customThe mixture was degassed
2. customby bubbling nitrogen through for 10 min
3. customThe tube was irradiated with microwave at 100° C. for 10 min
4. customthen partitioned between water (20 mL) and EtOAc (20 mL)
5. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
6. washThe combined organic phases were washed with saturated aqueous NaCl (40 mL)
7. dry with materialThe organic phase was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by column chromatography (eluent: acetone in hexanes 0% -30%)