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

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate (2.55 g, 7.16 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (1.0 g, 6.51 mmol) in 1,4-dioxane (20 mL) was added CuI (494 mg, 2.6 mmol), K2CO3 (3.6 g, 26 mmol), and N1,N2-dimethylethane-1,2-diamine (460 mg, 5.2 mmol). The mixture was heated at 100° C. for 3 hours, which was monitored by LC-MS. The reaction mixture 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)-1,4-diazepane-1-carboxylate as a yellow solid (1.6 g, 57%). MS (ESI) m/z: 429[M+H]+.

Provenance & Evidence