Реакция #1899323

Уравнение реакции

5-(1,3-Dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid

magnesium sulfate

pinacol

→

5-(1,3-dioxolan-2-yl)-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Выход 95.1%

Растворители

PhMe

Условия реакции

Обработка

1. 1
   ФильтрацияThe suspension was filtered
2. 2
   Промывкаthe solid was washed with EtOAc
3. 3
   ПромывкаThe filtrate was washed with brine (2×200 mL)
4. 4
   Сушкаthe organic phase was dried over sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеdried

Методика

5-(1,3-Dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid (14.56 g, 68.4 mmol) was suspended in PhMe (300 mL) and anhydrous magnesium sulfate (41.223 g, 342 mmol) and pinacol (8.27 g, 70.0 mmol) were added. The reaction was stirred under nitrogen at room temperature over the weekend. The suspension was filtered, and the solid was washed with EtOAc. The filtrate was washed with brine (2×200 mL), and the organic phase was dried over sodium sulfate, filtered, concentrated and dried to give 19.19 g of 5-(1,3-dioxolan-2-yl)-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine as a light yellow powder. 1H NMR (CDCl3, 400 MHz) δ 8.39 (d, J=2.54 Hz, 1H); 8.28 (dd, J=8.02 Hz, 2.54 Hz, 1H); 5.84 (s, 1H); 4.17-4.04 (m, 4H); 1.37 (s, 12H).

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