Cesium carbonate → 5-(1,1-Dimethylethyl)-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridine

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Reaction Conditions

Reaction Steps

To a solution of 1,7-dihydro-5-(1,1-dimethylethyl)-1-phenylpyrazolo[3,4-b]pyridin-6-one (26 mg, 0.097 mmol) in dry N,N-dimethylformamide (4 ml) under nitrogen was added cesium carbonate (95 mg, 0.29 mmol) followed by 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (25 mg, 0.15 mmol). The reaction mixture was heated at 60° C. for 17 h. The mixture was then allowed to cool and partitioned between water and diethyl ether. The aqueous phase was extracted a second time with diethyl ether and the combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a white solid (25 mg, 71%), m.p. 143-145° C. δH (400 MHz; CDCl3) 1.40 (9H, s), 3.93 (2H, s), 5.69 (1H, s), 7.29-7.32 (1H, m), 7.49-7.53 (2H, m), 7.93 (1H, s), 7.98 (1H, s), 8.05 (1H, s), 8.19-8.21 (2H, m); m/z (ES+) 363 (M+H+)

Provenance & Evidence