1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 5-(4-(2-(t-Butyldimethylsilyloxy)ethyl)piperidin-1-yl)-2-chloropyridine

関与物質

役割	名称	HCID	仕込み量
反応物	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
反応物	2-Chloro-5-iodopyridine	HCID 4397176	—
反応物	4-Piperidineethanol TBS	HCID 16220759	—
反応物	Sodium t-butoxide	HCID 23676156	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	5-(4-(2-(t-Butyldimethylsilyloxy)ethyl)piperidin-1-yl)-2-chloropyridine	HCID 58299843	40.2%

反応条件

温度	80 °C

反応手順

2-chloro-5-iodopyridine (1.00 g, 4.18 mmol), compound 292 (1.02 g, 4.18 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.191 g, 0.209 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.242 g, 0.418 mmol), and sodium t-butoxide (0.803 g, 8.35 mmol) were dissolved in 20 mL dioxane. The reaction was purged with argon and heated at 80° C. for 16 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes/0-10% ethyl acetate) afforded compound 293 as a beige solid (597 mg, 40%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08841312B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-894b6f7d240e44efa386e0555428b34d
出典メモ	uspto-grants-2014_09