Potassium Phosphate, Tribasic → tert-butyl 4-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

関与物質

役割	名称	HCID	仕込み量
反応物	Potassium Phosphate, Tribasic	HCID 62657	—
反応物	Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate	HCID 4642098	—
反応物	2-(3-(3-Chloropyrazin-2-yloxy)azetidin-1-yl)quinoline	HCID 58547697	—
触媒	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
溶媒	Water	HCID 962	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	tert-butyl 4-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate	HCID 58547770	65%

反応条件

温度	110 °C

反応手順

To a solution of 2-(3-((3-chloropyrazin-2-yl)oxy)azetidin-1-yl)quinoline (see PREPARATION P2.6; 624 mg, 2.0 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (618 mg, 2.0 mmol) and K3PO4 (848 mg, 4.0 mmol) in 1,4-dioxane (20 mL) and H2O (4 mL) was added Pd(dppf)Cl2 (146 mg, 0.2 mmol) then the reaction mixture was stirred at 110° C. under N2 atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with CH2Cl2 (50 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give tert-butyl 4-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (600 mg, 1.3 mmol, yield 65%). ESI-MS (M+1): 460 calc. for C26H29N5O3 459.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08497265B2
出典データセット	uspto-grants-2013_07
ORD ID	ord-201891bc57014dffb405a3e26b9e3c0c
出典メモ	uspto-grants-2013_07