Sodium Bicarbonate → tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

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A mixture of tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (427 mg, 1.0 mmol), pyrimidin-5-ylboronic acid (372 mg, 3.0 mmol), PdCl2(dppf) (73 mg, 0.1 mmol), and aq. Solution of NaHCO3 (318 mg, 3.0 mmol) in 1,4-dioxane (5.0 mL) in a sealed tube was purged with nitrogen and stirred at 100° C. for 16 hours. After it was cooled to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography using petroleum ether:EtOAc (5:1˜1:1) as eluting solvents to afford tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as yellow solid (350 mg, yield 74%). ESI (MS) m/z=473 [M+H]+

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