Реакция #1936681

Уравнение реакции

4-(adamantan-1-ylmethoxy)-3-bromobenzonitrile

potassium carbonate

(2-methoxypyridin-3-yl)boronic acid

→

title compound

Выход 98.8%

4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile

Выход 98.8%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Другоеwas degassed three times with nitrogen
2. 2
   Другоеthe reaction mixture was degassed three further times with nitrogen
3. 3
   Температураthe reaction was cooled to ambient temperature
4. 4
   Другоеthe reaction was degassed three times with nitrogen
5. 5
   Температураheated at 90° C. for further 7 h
6. 6
   ТемператураAfter cooling to ambient temperature
7. 7
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate (200 mL)
8. 8
   Промывкаwashed with water and brine
9. 9
   Сушкаdried over anhydrous sodium sulfate
10. 10
    Концентрированиеconcentrated in vacuo
11. 11
    ДругоеPurification of the residue by column chromatography (15% ethyl acetate in hexanes)

Методика

A reaction mixture of 4-(adamantan-1-ylmethoxy)-3-bromobenzonitrile (1.04 g, 3.00 mmol), potassium carbonate (1.00 g, 7.20 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.92 g, 6.00 mmol) in dioxane (30 mL) was degassed three times with nitrogen, then tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol) was added and the reaction mixture was degassed three further times with nitrogen. The resulting mixture was heated at 90° C. for 19 h, and then the reaction was cooled to ambient temperature, (2-methoxypyridin-3-yr)boronic acid (0.46 g, 3.00 mmol) and tetrakis(triphenylphosphfne)-pailadium(0) (0.09 g, 0.08 mmol) were added and the reaction was degassed three times with nitrogen and heated at 90° C. for further 7 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with water and brine; dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography (15% ethyl acetate in hexanes) afforded the title compound as a colorless solid (1.11 g, 98%): 1H NMR (300 MHz, CDCl3) δ 8.20-8.16 (m, 1H), 7.62-7.48 (m, 3H), 6.96-6.91 (m, 2H), 3.87 (s, 3H), 3.48 (s, 2H), 1.89 (br s, 3H), 1.68-1.35 (m, 12H); MS (ES+) m/z: 375.2, (M+1).

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