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

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-4-hydroxyazepane-1-carboxylate (792 mg, 2.4 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (300 mg, 1.94 mmol) in 1,4-dioxane (20 mL) was added CuI (150 mg, 0.78 mmol), K2CO3 (1.08 g, 7.8 mmol), and N1,N2-dimethylethane-1,2-diamine (138 mg, 1.56 mmol). The mixture was heated at 100° C. for 3 hours, which was monitored by LCMS. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (4/1) to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-4-hydroxyazepane-1-carboxylate as a white solid (550 mg, 58%). MS (ESI) m/z: 444 [M+H]+.

Provenance & Evidence