Sodium Carbonate → 2-chloro-3-(3,6-dihydro-2H-pyran-4-yl)pyridine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Bromo-2-chloropyridine	HCID 693324	—
Reactant	1-(3,6-Dihydro-2H-pyran-4-yl)-3,3,4,4-tetramethylborolane	HCID 67478747	—
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	2-chloro-3-(3,6-dihydro-2H-pyran-4-yl)pyridine	HCID 58547750	131.5%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a solution of 3-bromo-2-chloropyridine (4 g, 10.8 mmol), 4-(3,3,4,4-tetramethyl-borolan-1-yl)-3,6-dihydro-2H-pyran (5.7 g, 13.1 mmol) and Na2CO3 (2.28 g, 21.6 mmol) in 1,4-dioxane (60 mL) and H2O (6 mL) was added Pd(dppf)Cl2 (410 mg, 0.56 mmol). The reaction mixture was stirred at 110° C. under N2 for overnight. The reaction mixture was filtered through CELITE® and washed CH2Cl2. The organic layers were concentrated to give the crude product which was purified by silica gel column chromatography to give the title compound (3.5 g, 14.2 mmol, 70% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08497265B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-60d5635f8c094ca89567576722cecb25
Source note	uspto-grants-2013_07