反应详情

温度

65 °C

A round-bottomed flask was charged with 6-Bromo-[1,3]dioxolo[4,5-b]pyridine IM13 (1.74 g, 8.61 mmol) in DMF (25 ml) under N2 and tributyl(1-ethoxyvinyl)tin (3.65 ml, 10.8 mmol) was added. Tetrakistriphenylphosphinepalladium(0) (0.50 g, 0.43 mmol) was added and the solution was stirred at 65° C. overnight. The mixture was added to water and EtOAc and the phases were separated. The org phase was washed with brine, dried (MgSO4) filtered and was rotovaped. The residue was dissolved in THF (100 ml), and a mixture of water (15 ml) and conc. HCl (2.5 ml) was added and the solution was stirred at rt 5 min. The solution was added to brine and sat NaHCO3 solution was added until the solution was slightly alkaline. The org Phase was extracted with EtOAc and the phases were separated. The org phase was washed with brine, dried (MgSO4) filtered and was rotovaped. The residue was redissolved in THF (10 ml) EtOAc (20 ml) and heptanes (20 ml). The mixture was concentrated until 25 ml remained and cooled in ice. A solid precipitated and was collected by filtration. Yield: 0.942 g (66%) of IM21. 1H-NMR (500 MHz, DMSO) δ 8.47 (s, 1H), 8.54 (s, 1H), 6.27 (s, 2H), 2.53 (s, 3H).

1. customthe phases were separated
2. washThe org phase was washed with brine
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. dissolutionThe residue was dissolved in THF (100 ml)
6. additiona mixture of water (15 ml) and conc. HCl (2.5 ml)
7. additionwas added
8. stirringthe solution was stirred at rt 5 min
9. additionThe solution was added to brine
10. additionwas added until the solution
11. extractionThe org Phase was extracted with EtOAc
12. customthe phases were separated
13. washThe org phase was washed with brine
14. dry with materialdried (MgSO4)
15. filtrationfiltered
16. dissolutionThe residue was redissolved in THF (10 ml) EtOAc (20 ml)
17. concentrationThe mixture was concentrated until 25 ml
18. temperaturecooled in ice
19. customA solid precipitated
20. filtrationwas collected by filtration