Reaktion #48211

Reaktionsgleichung

Sodium hydride

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

ethyl acetate

1-benzyloxy-4-chloromethyl-2-fluoro-benzene

→

4-[(4-Benzyloxy-3-fluoro-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe mixture was transferred into a separation funnel
3. 3
   Waschenwashed with water (2×50 mL) and brine (30 mL)
4. 4
   TrocknenThe organic layer was dried over sodium sulphate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Temperaturheated
7. 7
   Temperaturto reflux for 5 minutes
8. 8
   FiltrationThe white solid was filtered off
9. 9
   Sonstigedried under high vacuum

Vorschrift

Sodium hydride (600%, 400 mg, 10.0 mmol) was added to a solution of 4-([1,2,4]triazol-4-ylamino)-benzonitrile (1.8-52 g, 10.0 mmol) in DMF (50 mL) at room temperature. The mixture was stirred for 1 h at this temperature and 1-benzyloxy-4-chloromethyl-2-fluoro-benzene (CAB03018, 2.51 g, 10.0 mmol) was added. The reaction mixture was stirred overnight and ethyl acetate (200 mL) and water (50 mL) were added. The mixture was transferred into a separation funnel and washed with water (2×50 mL) and brine (30 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The residue was suspended in 2-propanol (40 mL) and heated to reflux for 5 minutes. The white solid was filtered off after cooling to room temperature and dried under high vacuum. Yield: 3.12 g (78%). 1H-NMR (400 MHz, d6-DMSO) δ=4.97 (s, 2H), 5.12 (s, 2H), 6.73 (d, J=9.0 Hz, 2H), 7.01 (dd, J=8.2, 1.2 Hz, 1H), 7.16 (dd, J=8.6, 8.6 Hz 1H), 7.21 (dd, J=8.6, 2.4 Hz, 1H), 7.30-7.44 (m, 5H), 7.75 (d, =9.0 Hz, 2H), 8.80 (s, 2H). LRMS (FAB+): 400.1 (100, [M+H]+).

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