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

関与物質

役割	名称	HCID	仕込み量
反応物	N,N'-Dimethylethylenediamine	HCID 8070	—
反応物	Potassium Carbonate	HCID 11430	—
反応物	6-Chloro-1H-pyrazolo(4,3-c)pyridine	HCID 56932109	—
反応物	tert-Butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate	HCID 70700340	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate	HCID 86707047	57.3%

反応条件

温度	100 °C

反応手順

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 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)-1,4-diazepane-1-carboxylate as a yellow solid (1.6 g, 57%). MS (ESI) m/z: 429 [M+H]+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09434725B2
出典データセット	uspto-grants-2016_09
ORD ID	ord-1943d0852c264f4d8db42f973130b916
出典メモ	uspto-grants-2016_09