Sodium Carbonate → 3-(3,6-Dihydro-2H-pyran-4-YL)-2,5-difluoro-pyridine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester	HCID 11218053	—
Reactant	3-Bromo-2,5-difluoropyridine	HCID 14600696	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-(3,6-Dihydro-2H-pyran-4-YL)-2,5-difluoro-pyridine	HCID 58548658	90.2%

Reaction Steps

To a solution of 3-bromo-2,5-difluoro-pyridine (4.1 g, 20.8 mmol) in dioxane (60 mL) was treated with Na2CO3 (4.4 g, 41.6 mmol) in 20 mL of H2O as a solution, followed by additional of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (4.8 g 22.9 mmol) and Pd(dppf)Cl2 (761 mg). The resulting mixture was heated at refluxing overnight under N2 atmosphere. TLC showed that most of the staring materials were consumed. The solution was filtered and the filtrate was concentrated to get a residue, which was purified by silica gel chromatography to give the product (3.7 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08952037B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-f3fab060d57f4e509e24eee64a56e01f
Source note	uspto-grants-2015_02