Dichloromethane → N-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(6-formylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

関与物質

役割	名称	HCID	仕込み量
反応物	Dichloromethane	HCID 6344	—
反応物	Cesium carbonate	HCID 10796	—
反応物	5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbaldehyde	HCID 44754839	—
反応物	7-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide	HCID 71283181	—
触媒	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
溶媒	Water	HCID 962	—
溶媒	1,2-Dimethoxyethane	HCID 8071	—
生成物	N-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(6-formylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide	HCID 86695680	—

反応条件

温度	100 °C

反応手順

A mixture comprising 7-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (Intermediate 3A) (2.7 g, 5.36 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinaldehyde (1.375 g, 5.90 mmol) and cesium carbonate (6.99 g, 21.46 mmol) in DME (30 ml) and water (3 ml) was treated with PdCl2(dppf).CH2Cl2 adduct (0.219 g, 0.268 mmol). The mixture was placed under nitrogen and heated at 100° C. for 1 hr. The resulting mixture was concentrated in vacuo and the residue was dissolved in 10% trifluoroethanol/CHCl3. The organics were washed with water and NaHCO3 and concentrated in vacuo. Purification by chromatography on silica eluting with 0-30% 2M NH3 in MeOH/DCM afforded the title product;

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08883819B2
出典データセット	uspto-grants-2014_11
ORD ID	ord-3b77c0cc052b48ac95722199e5750bae
出典メモ	uspto-grants-2014_11