تفاعل #48215

معادلة التفاعل

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

المذيبات

DMF

water

ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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]+).

المصدر