反应详情

温度

100 °C

A vigorously stirred mixture of the tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (1-4) (1.40 g, 4.53 mmol), methyl(2-bromo-5-chlorophenyl)acetate (1-2) (1.31 g, 4.98 mmol), potassium phosphate tribasic (2.85 g, 13.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.262 g, 0.227 mmol) in N,N-dimethylformamide (22 mL) was degassed via three vacuum/nitrogen ingress cycles and then heated at 100° C. for approximately 18 h. After cooling to room temperature, the reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% ethyl acetate/hexanes as eluent) afforded 1-5 (0.967 g) as a colorless oil.

1. customwas degassed via three vacuum/nitrogen ingress cycles
2. temperatureAfter cooling to room temperature
3. additionthe reaction mixture was poured into water
4. extractionextracted three times with ethyl acetate
5. washThe combined organic extracts were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% ethyl acetate/hexanes as eluent)