N-(2-(p-bromophenoxy)ethyl)pyrrolidine → [5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

참여 물질

역할	이름	HCID	투입량
반응물	N-(2-(p-bromophenoxy)ethyl)pyrrolidine	HCID 70657	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	Sodium t-butoxide	HCID 23676156	—
반응물	5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine	HCID 59589684	—
촉매	Dimethylacetamide	HCID 31374	—
촉매	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
용매	1,4-Dioxane	HCID 31275	—
생성물	[5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine	HCID 59589976	—

반응 조건

온도	150 °C

반응 단계

In a microwave vial, 5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.05 g, 0.17 mmol), 1-[2-(4-bromophenoxyl)ethyl]-pyrrolidine (0.068 g, 0.251 mmol), bis(dibenzylideneacetone)palladium (0.005 g, 0.008 mmol), Xantphos (0.01 g, 0.017 mmol) and sodium tert-butoxide (0.033 g, 0.335 mmol) were added successively. Dioxane (1.2 mL) and dimethylacetamide (2 drops) were added and the vial was sealed and heated in the microwave (150° C., 10 min). The crude was purified using an SCX cartridge, by washing with methanol and releasing the compound with 2M ammonia in methanol. After concentration under reduced pressure, the crude was purified by preparatory LCMS. LCMS Method: 2: RT: 2.52 min, M1:488 [M+1].

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09394301B2
출처 데이터셋	uspto-grants-2016_07
ORD ID	ord-1132b52d9f7d4b1a8a48765fe32d55a2
출처 메모	uspto-grants-2016_07