Reacción #48215

Ecuación de reacción

benzoic acid 5-bromomethyl-2-fluoro-phenyl ester

Sodium

hydride

4-([1,2,4]triazol-4-ylamino)-benzonitrile

→

Benzoic Acid 5-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]methyl}-2-fluoro-phenyl Ester

Disolventes

DMF

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe mixture was transferred into a separation funnel
3. 3
   Lavadowashed with water (2×50 mL) and brine (20 mL)
4. 4
   SecadoThe organic layer was dried over sodium sulphate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by column chromatography (EtOAc, Rf: 0.32)
7. 7
   Otroto give a white solid

Procedimiento

Sodium, hydride (60%, 200 mg, 5.0 mmol) was added to a solution of 4-([1,2,4]triazol-4-ylamino)-benzonitrile (926 mg, 5.0 mmol) in DMF (20 mL) at r.t. The mixture was stirred for 1 h at this temperature and benzoic acid 5-bromomethyl-2-fluoro-phenyl ester (CAB02146, 1.55 g, 5.0 mmol) was added. The reaction mixture was stirred overnight and ethyl acetate (75 mL) and water (50 mL) were added. The mixture was transferred into a separation funnel and washed with water (2×50 mL) and brine (20 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc, Rf: 0.32) to give a white solid. Yield: 1.16 g (56%). 1H-NMR (400 MHz, CDCl3) δ=4.91 (s, 2H), 6.67 (d, J=9.0 Hz, 2H), 7.07 (ddd, J=8.2, 4.3, 2.0 Hz, 1H), 7.18 (dd, J=9.4, 8.6 Hz, 1H), 7.24 (dd, J=7.0, 2.3 Hz, 1H), 7.49-7.56 (m, 2H), 7.58 (d, J=9.0 Hz, 2H), 7.62-7.70 (m, 1H), 8.15-8.20 (m, 2H), 8.21 (s, 2H). LRMS (FAB+): 414.2 (100, [M+H]+).

Fuente