反应详情

To a 25 mL flask containing 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-one (SM-1a, 50.0 mg, 0.19 mmol) was added 2-bromo-4-methyl pyrimidine (33.6 mg, 0.16 mmol) and sodium carbonate (23 mg, 0.76 mmol). The mixture was dissolved in 2 mL DME and 0.5 mL water. The mixture was purged with nitrogen for 15 minutes. Pd(dppf)Cl2 (2.9 mg, 5 mol %) was added and the solution was degassed for an additional 15 minutes. The reaction was heated under reflux for 16 hours. The reaction was concentrated to dryness and was partitioned between ethyl acetate and water. The water layer was extracted with ethyl acetate and the combined organic layers were washed twice with water and once with brine. The solution was dried over anhydrous sodium sulfate, filtered and concentrated. The final product was purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Corp., Lincoln, Nebr.) eluting with 0-50% ethyl acetate in heptanes. The product was obtained as a white solid (SM-1e, 8.7 mg, 20%). MS (ES+) 225.2 (M+H+). 1H NMR (CDCl3) δ 2.61 (s, 3H), 2.74-2.78 (m, 2H), 3.20 (t, 2H), 7.15 (d, 1H), 7.85 (d, 1H), 8.53 (d, 1H), 8.59 (s, 1H), 8.75 (d, 1H).

1. customThe mixture was purged with nitrogen for 15 minutes
2. additionPd(dppf)Cl2 (2.9 mg, 5 mol %) was added
3. customthe solution was degassed for an additional 15 minutes
4. temperatureThe reaction was heated
5. temperatureunder reflux for 16 hours
6. concentrationThe reaction was concentrated to dryness
7. customwas partitioned between ethyl acetate and water
8. extractionThe water layer was extracted with ethyl acetate
9. washthe combined organic layers were washed twice with water and once with brine
10. dry with materialThe solution was dried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe final product was purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Corp., Lincoln, Nebr.)
14. washeluting with 0-50% ethyl acetate in heptanes
15. customThe product was obtained as a white solid (SM-1e, 8.7 mg, 20%)