反应详情

Add bis(neopentyl glycolato)diboron (4.2 g, 18.59 mmol), 5-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl acetate (2.33 g, 4.21 mmol), palladium (II) acetate (0.199 g, 886.38 μmol), cesium fluoride (5.21 g, 34.30 mmol), tricyclohexylphosphine (0.41 g, 1.40 mmol) and acetonitrile (50 mL) to a round bottom flask. Reflux the mixture with stirring for 1 hour under a nitrogen atmosphere. Cool the mixture, filter and wash the solids with acetonitrile. Concentrate the combined filtrate and washes. Suspend the resulting residue in diethyl ether (40 mL) and sonicated for 30 minutes. Remove the precipitate by filtration and concentrate the filtrate to obtain the crude intermediate. Add diethanolamine (405.25 μL, 4.21 mmol) to a solution of the crude intermediate in ether (50 mL). Stir the mixture for 1 hour. Decant the organic layer and dissolve the remaining residue in methanol (20 mL) and 10 mL of water. Add concentrated HCl (2 mL; 24 mmol) and stir the resulting mixture for 16 hours. Concentrate the mixture to remove MeOH. Extract the aqueous residue 3 times with dichloromethane. Combine the extracts, dry over sodium sulfate, filter, and concentrate to dryness. Purify the residue by flash chromatography on silica to obtain the title compound. (0.6 g, 1.47 mmol).

1. temperatureReflux the mixture
2. temperatureCool the mixture
3. filtrationfilter
4. washwash the solids with acetonitrile
5. concentrationConcentrate the combined filtrate and washes
6. customsonicated for 30 minutes
7. customRemove the precipitate
8. filtrationby filtration
9. concentrationconcentrate the filtrate
10. customto obtain the crude intermediate
11. stirringStir the mixture for 1 hour
12. customDecant the organic layer
13. dissolutiondissolve the remaining residue in methanol (20 mL)
14. stirringstir the resulting mixture for 16 hours
15. concentrationConcentrate the mixture
16. customto remove MeOH
17. extractionExtract the aqueous residue 3 times with dichloromethane
18. dry with materialdry over sodium sulfate
19. filtrationfilter
20. concentrationconcentrate to dryness
21. customPurify the residue by flash chromatography on silica