反应详情

温度

90 °C

Stir a solution of 4 g (14.35 mmol) of methyl 5-iodo-6-oxo-1,6-dihydropyridine-3-carboxylate and 6.42 g (18.64 mmol) of 2-[3-(benzyloxy)-4-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a mixture of 160 mL of dimethoxyethane (DME), 80 mL of EtOH and 120 mL of a saturated aqueous solution of NaHCO3 for 15 minutes under argon, then add 662 mg of Pd(PPh3)4 and heat the reaction mixture for 4 h 30 min at 90° C. After concentration under reduced pressure, distribute the residue obtained in a mixture of 200 mL of DCM and 10 mL of water. Extract the aqueous phase again with 100 mL of DCM, combine the organic phases, dry over MgSO4, filter and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a DCM/methanol gradient from 0 to 2% of methanol. After concentration under reduced pressure, solidify the residue in a 5/95 methanol/ether mixture, then filter and wash with ether. We thus obtain 1.99 g of methyl 5-[3-(benzyloxy)-4-chlorophenyl]-6-oxo-1,6-dihydropyridine-3-carboxylate in the form of a beige solid.

1. concentrationAfter concentration under reduced pressure
2. customobtained in a mixture of 200 mL of DCM and 10 mL of water
3. extractionExtract the aqueous phase again with 100 mL of DCM
4. dry with materialdry over MgSO4
5. filtrationfilter
6. concentrationconcentrate under reduced pressure
7. customPurify the residue
8. customobtained by silica gel column chromatography
9. washeluting with a DCM/methanol gradient from 0 to 2% of methanol
10. concentrationAfter concentration under reduced pressure
11. filtrationfilter
12. washwash with ether