Methanol → 2-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)pyridine

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	p-Chlorophenylboric acid	HCID 17810664	—
Reactant	5-Bromo-2-((tert-butyldimethylsilyl)ethynyl)pyridine	HCID 66611213	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)pyridine	HCID 69058350	—

Reaction Steps

250 mL of MeOH, 220 mL of 2N sodium carbonate (Na2CO3) solution, and 1.80 g (2.46 mmol) of PdCl2(dppf) are added to a solution of 59.5 g (201.0 mmol) of 5-bromo-2-[(tert-butyldimethylsilanyl)ethynyl]pyridine and 36.5 g (233.4 mmol) of 4-chlorophenylboric acid in 600 mL of 1,4-dioxane and the mixture is refluxed for 1 hour. The reaction mixture is evaporated down in vacuo and diluted with EtOAc. The organic phase is washed with water and semisaturated sodium bicarbonate (NaHCO3) solution, dried over sodium sulfate, and evaporated down in vacuo. The residue is purified by column chromatography (silica gel, Cyc/EtOAc 9:1). Yield: 38.5 g (58% of theoretical); C19H22ClNSi (M=327.923); calc.: molpeak (M+H)+: 328/330 (Cl); found: molpeak (M+H)+: 328/330 (Cl); Rf value: 0.60 (silica gel, Cyc/EtOAc 8:1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07524862B2
Source dataset	uspto-grants-2009_04
ORD ID	ord-a474e408b4464b59b5097214d30633bc
Source note	uspto-grants-2009_04