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

関与物質

役割	名称	HCID	仕込み量
反応物	N-(2-(p-bromophenoxy)ethyl)pyrrolidine	HCID 70657	—
反応物	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
反応物	Sodium t-butoxide	HCID 23676156	—
反応物	5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine	HCID 59589684	—
触媒	Dimethylacetamide	HCID 31374	—
触媒	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	[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	—

反応条件

温度	150 °C

反応手順

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-bromophenoxy)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, MI: 488 [M+1].

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09012633B2
出典データセット	uspto-grants-2015_04
ORD ID	ord-5c5e2e70bf91492fbd9b29cdbe57ac50
出典メモ	uspto-grants-2015_04