Cesium carbonate → Dimethyl 5-(4-pyridyl)-1-methyl-6-oxo-1,6-dihydropyridine-3,4-dicarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	(Pyridin-4-yl)boronic acid	HCID 2734379	—
Reactant	1-Methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-pyridine-5-carboxylic acid	HCID 90422009	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	Dimethyl 5-(4-pyridyl)-1-methyl-6-oxo-1,6-dihydropyridine-3,4-dicarboxylate	HCID 125500102	40%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a mixture of compound (4) (3.5 g, 13.5 mmol), pyridine-4-yl-boronic acid (4.9 g, 40.4 mmol), Pd(dppf)Cl2 (1.1 g, 1.3 mmol) and Cs2CO3 (13.1 g, 40.4 mmol) in DME/water (4/1, 80 ml) was stirred at 90° C. overnight. The solution was concentrated and purified by column chromatography on silica gel (DCM/MeOH=100:1) to give title compound as off-white solid (1.6 g, 40%). LC-MS (ESI+): m/e 303 (M+H)+, Rt: 0.561 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09163019B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-ea74dd792497452e9b3a8837eb31d92d
Source note	uspto-grants-2015_10