Реакция #1490840

Уравнение реакции

(S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

3,4-difluorophenylboronic acid

K3PO4

→

(S)-methyl 2-(3,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Выход 48.2%

Растворители

dioxane

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with dichloromethane (3×30 mL)
2. 2
   Сушкаdried over anhydrous magnesium sulfate
3. 3
   Концентрированиеconcentrated under reduced pressure
4. 4
   Другоеto afford a residue, which
5. 5
   Другоеwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Методика

To a solution of (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (195 mg, crude) in dioxane (3 mL) was added 3,4-difluorophenylboronic acid (130 mg, 0.80 mmol), K3PO4 (180 mg, 0.8 mmol), Pd(PPh3)4 (28 mg, 0.024 mmol) and water (5 drops) under a nitrogen atmosphere. After stirring 1 h at 90° C., the reaction mixture was dissolved in water (100 mL), extracted with dichloromethane (3×30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford a residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(3,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a light yellow solid (86.0 mg).

Источник