Ethanol → 5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)-4-ethoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine

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A solution of 5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine (10 mg, 0.022 mol) in EtOH (1 mL) is treated with tert-butyl nitrite (23 mg, 0.22 mol) and heated to 80° C. for 16 hours. After cooling down to room temperature, the mixture is concentrated and purified by preparative thin layer chromatography to provide 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine (Example 4) and 5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)-4-ethoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine is also obtained as side product (Example 5). Example 4: 1H NMR (CDCl3) δ(ppm) 8.35 (d, 2H), 8.29 (s, 1H), 8.14 (s, 1H), 7.48(t, 2H), 7.37(d, 1H), 7.28 (t, 1H), 7.23-7.17(m, 4H), 7.11(d, 2H); HPLC-MS calculated for C24H14C13N3 (M+H+): 450.0. Found: 450.2. Example 5: 1H NMR (CDCl3) δ(ppm) 8.36(s, 1H), 8.30 (d, 2H), 7.48 (t, 2H), 7.32 (d, 1H), 7.29 (d, 1H), 7.18 (d, 2H), 7.05-7.14(m, 4H), 4.68 (q, 2H), 1.42 (t, 3H); HPLC-MS calculated for C26H18C13N3O (M+H+): 494.1, Found: 494.2.

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