Cesium carbonate → 1,1-Dimethylethyl (2-{4-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)carbamate

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	Binap, (A+-)-	HCID 634876	—
반응물	1-(2-N-Boc-aminoethyl)piperazine	HCID 1514401	—
반응물	8-Bromo-7-fluoro-2-methoxy-1,5-naphthyridine	HCID 45480320	—
촉매	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
용매	1,4-Dioxane	HCID 31275	—
생성물	1,1-Dimethylethyl (2-{4-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)carbamate	HCID 57599576	41.6%

반응 조건

온도	100 °C

반응 단계

In a sealed tube, 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (1.1 g, 4.3 mmol), 1,1-dimethylethyl [2-(1-piperazinyl)ethyl]carbamate (1 g, 4.3 mmol), Pd2dba3 (271 mg, 0.262 mmol), rac-Binap (163 mg, 0.262 mmol), Cs2CO3 (2.98 mg, 9.2 mmol) and 18-C-6 (115 mg, 0.436 mmol) in dioxane (22 mL) were combined and flushed with N2. After 15 min, the tube was sealed and heated to 100° C. while stirring rapidly. After 12 h, the solution was filtered, concentrated and the residue purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) yielding the title compound (725 mg, 41%) as an orange oil: LCMS (ES) m/e 406 (M+H)+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07511035B2
출처 데이터셋	uspto-grants-2009_03
ORD ID	ord-3c2b57db026d4b52aa151ef77a6cd671
출처 메모	uspto-grants-2009_03