反应详情

温度

90 °C

A vigorously stirred suspension of methyl 2-(6-amino-5-iodopyridin-3-yl)-2-methylpropanoate (4.61 g, 14.4 mmol), (S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane (4.98 g, 17.3 mmol), Pd(dppf)Cl2·CH2Cl2 (0.59 g, 0.72 mmol) LiCl (0.61 g, 14.4 mmol), Na2CO3 (3.82 g, 36.0 mmol) and N,N-dimethylformamide (60 mL) was degassed via three vacuum/nitrogen ingress cycles and the resulting mixture was heated at approximately 90° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate and filtered through celites washing copiously with ethyl acetate. The filtrate was poured into water and extracted with ethyl acetate (x3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (gradient elution; 20-25% ethyl acetate/hexanes as eluent) to give the title compound as a viscous oil (6.11 g).

1. customwas degassed via three vacuum/nitrogen ingress cycles
2. temperatureAfter cooling to ambient temperature
3. additionthe reaction mixture was diluted with ethyl acetate
4. filtrationfiltered through celites
5. washwashing copiously with ethyl acetate
6. additionThe filtrate was poured into water
7. extractionextracted with ethyl acetate (x3)
8. extractionThe combined organic extract
9. washwas washed with brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated in vacuo
12. customThe residue was purified by flash chromatography on silica gel (gradient elution; 20-25% ethyl acetate/hexanes as eluent)