Sodium Carbonate → tert-butyl 4-hydroxy-4-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)azepane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-4-hydroxyazepane-1-carboxylate (500 mg, 1.12 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (350 mg, 1.69 mmol), Pd(dppf)Cl2 (50 mg, 0.06 mmol), and aqueous solution of Na2CO3 (2.0 M, 2.0 mL) in 1,4-dioxane (30 mL) under nitrogen was stirred at 100° C. for 18 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/EtOAc (2/1) as eluting solvents to afford tert-butyl 4-hydroxy-4-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)azepane-1-carboxylate as a yellow oil (500 mg, 91%). MS (ESI) m/z: 490 [M+H]+.

Provenance & Evidence