Tri-tert-butylphosphine tetrafluoroborate → isopropyl 4-{[6-(2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate

関与物質

役割	名称	HCID	仕込み量
反応物	Tri-tert-butylphosphine tetrafluoroborate	HCID 2734635	—
反応物	1H,2H,3H-pyrrolo[3,2-b]pyridine	HCID 18771136	—
反応物	Potassium tert-butoxide	HCID 23665647	—
反応物	4-(6-Chloro-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester	HCID 46738288	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	Tetrahydrofuran	HCID 8028	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	isopropyl 4-{[6-(2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate	HCID 49848658	—

反応条件

温度	80 °C

反応手順

A mixture of 2b (100 mg, 0.33 mmol), potassium tert-butoxide (0.1 g, 2.7 eq), 1-1 (0.35 mmol, 1.05 eq), tris(dibenzylideneacetone)dipalladium (32 mg, 0.1 eq), tri-t-butylphosphonium tetrafluoroborate (40 mg, 0.4 eq) and dioxane (1 mL) was heated at 80° C. for 18 h in a sealed vial. After allowing the reaction to cool down to room temperature, THF was added and the mixture was filtered. The filtrate was concentrated under a stream of nitrogen and the residue was taken up with 1 mL of THF and purified by preparative HPLC to afford 2-1.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08481731B2
出典データセット	uspto-grants-2013_07
ORD ID	ord-f5e0ef3303a4442f8055515fed972946
出典メモ	uspto-grants-2013_07