Реакция #58365

Уравнение реакции

sodium carbonate

4-chloro-8-(2,6-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

4-fluorobenzeneboronic acid

→

title compound

Выход 63.0%

8-(2,6-Difluorophenyl)-4-(2-methylphenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Выход 63.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was irradiated with microwave at about 150° C. for about 20 min
2. 2
   Фильтрацияfiltered
3. 3
   Другоеthe filtrate evaporated
4. 4
   workup.DISSOLUTIONThe crude product was redissolved in ethyl acetate (10 mL)
5. 5
   ДругоеThe layers were separated
6. 6
   Сушкаthe organic layer was dried over magnesium sulphate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated
9. 9
   ДругоеThe crude product was purified by flash chromatography on silica gel with cyclohexane
10. 10
    workup.ADDITIONcontaining ethyl acetate (0 to 50%)

Методика

THF (10 mL) and 2M sodium carbonate (2 mL) were added to a mixture of 4-chloro-8-(2,6-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.34 g, 1.0 mmol, solid-supported tetrakis(triphenylphosphine)palladium(0) (0.39 g, 0.1 mmol) and 4-fluorobenzeneboronic acid (0.21 g, 1.5 mmol). The mixture was irradiated with microwave at about 150° C. for about 20 min, then filtered and the filtrate evaporated. The crude product was redissolved in ethyl acetate (10 mL) and water (10 mL). The layers were separated and the organic layer was dried over magnesium sulphate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with cyclohexane containing ethyl acetate (0 to 50%) to give the title compound (0.25 g, 63%). LC-MS m/z 396 (M+H)+, 3.55 min (ret time).

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