1,10-Phenanthroline → tert-butyl 4-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-Butyl 4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.12 g, 0.218 mmol, see Example 5), Cu(I)I (0.0416 g, 0.218 mmol), 1,10-phenanthroline (0.0393 g, 0.218 mmol), (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (0.812 mL, 6.55 mmol) and KF on Al2O3 (40%; 0.222 g, 1.53 mmol) in toluene (4 mL) was stirred at 120° C. for 75 hours. Ethyl acetate (10 mL) was then added, and the reaction was filtered through a pad of celite. The filtrate was then concentrated to dryness. The resulting residue was purified by chromatography (hexane:ethyl acetate, 1:1) to give tert-butyl 4-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.068 g, 56%) as a solid. MS APCI (+) m/z 554.4 detected.

Provenance & Evidence