N,N'-Dimethylethylenediamine → tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)Pyridine-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate (550 mg, 1.48 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (207 mg, 1.34 mmol) in 1,4-dioxane (20 mL) was added CuI (102 mg, 0.54 mmol), K2CO3 (743 g, 5.4 mmol), and N1,N2-dimethylethane-1,2-diamine (95 mg, 1.08 mmol). The reaction mixture was heated at 100° C. for 3 hours, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (2/1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate as a light yellow solid (160 mg, 24.3%). MS (ESI) m/z: 445[M+H]+.

Provenance & Evidence