Реакция #157120

Уравнение реакции

5-bromo-3-nitropicolinonitrile

phenylboronic acid

1,4-dioxane

Na2CO3

→

titled compound

3-nitro-5-phenylpicolinonitrile

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was degassed by anhydrous N2 stream for 5 min
2. 2
   Промывкаwashed with water, brine
3. 3
   Сушкаdried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated under reduced pressure
6. 6
   Другоеto give crude product, which
7. 7
   Другоеwas triturated by DCM, ether, hexanes

Методика

5-bromo-3-nitropicolinonitrile (1 eq) and phenylboronic acid (1.5 eq) was mixed with 15 mL of 1,4-dioxane and 5 mL of 2 M Na2CO3 aqueous solution in a glass pressure tube. The reaction mixture was degassed by anhydrous N2 stream for 5 min followed by the addition of Pd(dppf)Cl2-DCM (0.1 eq). The reaction mixture was stirred at 100° C. for 3 hours. Then the mixture was diluted with 100 mL of ethyl acetate and washed with water, brine, then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was triturated by DCM, ether, hexanes to give the pure titled compound. LC/MS (m/z): 226.1 (MH+).

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