Cesium carbonate → 3-Chloro-5-{[5-chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A stirred suspension of 5-chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol (0.050 g, 0.173 mmol), 3-fluoro-5-chloro-benzonitrile (0.081 g, 0.518 mmol) and cesium carbonate (0.068 g, 0.207 mmol) in NMP (1.5 mL) was heated at 140° C. for 72 hours. The reaction mixture was then quenched with aqueous ammonium chloride (25 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2O, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2×100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to yield the title product. 1H NMR (DMSO d6) δ 7.90-7.88 (m, 1H), 7.80 (s, 1H), 7.79-7.75 (m, 1H), 7.60-7.55 (m, 2H), 7.40-7.35 (d, J=6.9 Hz, 2H), 6.95-6.88 (m, 2H), 5.80 (s, 2H), 3.71 (s, 3H).

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