Reacción #7109

Ecuación de reacción

NaOH

4-cyano-3-fluoro-bromobenzene

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

sodium carbonate

→

title compound

Rendimiento 36.9%

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

Rendimiento 36.9%

Disolventes

water

ethylene glycol dimethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 18 hours
2. 2
   Extracciónextracted with EtOAc (×3)
3. 3
   LavadoThe combined extracts were washed with water, brine
4. 4
   Secadodried (MgSO4)
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by column chromatography (SiO2, EtOAc, hexane)

Procedimiento

A solution of 4-cyano-3-fluoro-bromobenzene (0.63 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (1.0 g, 4.7 mmol) and sodium carbonate (1.0 g, 9.4 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 (0.35 g, 36%) as a yellow solid. mp: dec. @235° C.; 1H NMR (DMSO-d6) δ 10.5 (s, 1H), 7.9 (t, 1H, J=7.6 Hz), 7.9 (dd, 1H, J=1.4, 10.2 Hz), 7.3 (td, 2H, J=1.6, 6.5 Hz), 7.6 (dd, 1H, J=1.9, 6.3 Hz), 6.9 (d, 1H, J=8.1 Hz), 2.0–1.9 (m, 8H); MS [M−H]−=305.

Fuente