Diethyl Ether → tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

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Reaction Steps

1-(Chloromethyl)-4-methoxybenzene (0.219 mL, 1.61 mmol) was added to tert-butyl 4-(3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.575 g, 1.34 mmol) and K2CO3 (0.222 g, 1.61 mmol) in DMF (10 mL). The reaction was stirred at room temperature for 2 hours. Ether (30 mL) and water (10 mL) were 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 chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.59 g, 80%) as a solid. MS APCI (+) m/z 549.7 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.37 (d, J=5.2 Hz, 1H), 7.21 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 6.68 (d, J=5.2 Hz, 1H), 5.53 (s, 2H), 3.70 (s, 3H), 3.62 (m, 4H), 3.19 (m, 4H), 1.43 (s, 9H).

Provenance & Evidence