Реакция #7103

Уравнение реакции

NaOH

4-cyano-3-fluoro-bromobenzene

(spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid

sodium acetate

→

title compound

Выход 37.0%

5′-(4-Cyano-3-fluorophenyl)-spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one

Выход 37.0%

Растворители

water

ethylene glycol dimethyl ether

Условия реакции

Обработка

1. 1
   Температураto reflux for 18 hours
2. 2
   Экстракцияextracted with EtOAc (×3)
3. 3
   ПромывкаThe combined extracts were washed with water, brine
4. 4
   Сушкаdried (MgSO4)
5. 5
   Другоеevaporated
6. 6
   ДругоеThe residue was purified by column chromatography (SiO2, EtOAc, hexane)

Методика

A solution of 4-cyano-3-fluoro-bromobenzene (0.76 g, 3.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.3 g) in ethylene glycol dimethyl ether (15 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (1.4 g, 5.7 mmol) and sodium acetate (1.2 g, 11.4 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (×3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the title compound (0.45 g, 37%) as an off-white solid. mp: 258–260° C.; 1H NMR (DMSO-d6) δ 8.8 (s, 1H), 7.7–7.6 (m, 2H), 7.5 (td, 2H, J=0.9. 1.5, 5.7 Hz), 7.4 (dd, 1H, J=1.5, 8.8 Hz), 7.0 (d, 1H, J=8.1 Hz), 2.0–1.6 (m, 10H); MS (−)APCI [M−H]− @m/z 319.

Источник