반응 #48202

반응 방정식

ethyl acetate

Sodium hydride

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

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

→

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

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The mixture was transferred into a separation funnel
3. 3
   세척washed with water (2×50 mL) and brine (20 mL)
4. 4
   건조The organic layer was dried over sodium sulphate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by column chromatography (EtOAc, Rf: 0.31)
7. 7
   기타to give a white solid

실험 절차

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 hour at this temperature and benzoic acid 5-bromomethyl-2-chloro-phenyl ester (CAB02138, 1.63 g, 5.0 mmol) was added. The reaction mixture was stirred overnight and ethyl acetate (75 mL) was 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: 0.31) to give a white solid. Yield: 1.773 g (82%). 1H-NMR (400 MHz, CDCl3) δ=4.93 (s, 2H), 6.66 (d, 9.0 Hz, 2H), 7.06 (dd, J=8.2, 2.0 Hz, 1H), 7.27 (d, J=2.0 Hz, 1H), 7.45 (d, J=8.2 Hz, 1H), 7.47-7.58 (m, 4H), 7.60-7.69 (m, 1H), 8.16-8.21 (m, 2H), 8.24 (s, 2H). LRMS (FAB+): 430.1 (100, [M+H]+).

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