反応 #48215

反応方程式

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

溶媒

DMF

water

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The mixture was transferred into a separation funnel
3. 3
   洗浄washed with water (2×50 mL) and brine (20 mL)
4. 4
   乾燥The organic layer was dried over sodium sulphate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was purified by column chromatography (EtOAc, Rf: 0.32)
7. 7
   その他to give a white solid

実験手順

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]+).

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