Cesium carbonate → tert-Butyl 4-(5-(6-amino-5-chloropyrazin-2-yl)pyridin-2-yl)piperazine-1-carboxylate

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	4-Boc-1-(5-bromo-2-pyridyl)piperazine	HCID 11244775	—
반응물	6-Bromo-3-chloropyrazin-2-amine	HCID 56965723	—
촉매	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
용매	1,4-Dioxane	HCID 31275	—
생성물	tert-Butyl 4-(5-(6-amino-5-chloropyrazin-2-yl)pyridin-2-yl)piperazine-1-carboxylate	HCID 117732307	29%

반응 조건

온도	90 °C

반응 단계

Into a 2 L 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of compound 90e (42.8 g, 206 mmol) in 1,4-dioxane (1 L), compound 90b (80.0 g, 206 mmol), Pd(dppf)Cl2 (7.53 g, 10.3 mmol) and Cs2CO3 (167 g, 514 mmol). The reaction mixture was stirred overnight at 90° C. Upon cooling, the reaction was quenched with water (100 mL). The resulting mixture was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (100:3 v/v)) to obtain compound 90f as a yellow solid (23.0 g, 29% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C18H23ClN6O2: 391.2 (M+H). found 391.1.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09249163B2
출처 데이터셋	uspto-grants-2016_02
ORD ID	ord-136fcc35055b407f892d7e9a44fa65c5
출처 메모	uspto-grants-2016_02