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 (800 mg, 2.16 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (330 mg, 2.16 mmol) in 1,4-dioxane (25 mL) was added CuI (164 mg, 0.86 mmol), N1,N2-dimethylethane-1,2-diamine (240 mg, 2.7 mmol), and K2CO3 (894 mg, 6.48 mmol). The mixture was heated at 100° C., which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using DCM:MeOH (20:1˜10:1) 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 yellow solid (671 mg, 70%). MS (ESI) m/z: 445 [M+H]+.

Provenance & Evidence