Water → HCID 68760394, compound

Participants

Reaction Steps

A solution of tert-butyl 4-(5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.20 g, 0.398 mmol, see Example 1), Zn(CN)2 (0.0304 g, 0.259 mmol), Zn dust (0.00625 g, 0.0955 mmol), Pd2dba3 (0.00729 g, 0.00796 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (“dppf”) (0.00883 g, 0.0159 mmol) in dimethylacetamide (“DMA”; 5 mL) were heated at 110° C. for 20 hours. Ether (50 mL) and H2O (20 mL) were then added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate, 1:1) to give tert-butyl 4-(5-cyano-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.16 g, 89%) as a solid. MS APCI (+) m/z 449.1 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.47 (s, 1H), 7.20 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 5.51 (s, 2H), 3.88 (m, 4H), 3.70 (s, 3H), 3.58 (m, 4H).

Provenance & Evidence