Sodium Carbonate → HCID 58547847, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester	HCID 11218053	—
Reactant	HCID 58547976	HCID 58547976	—
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	HCID 58547847	HCID 58547847	77.7%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a solution tert-butyl 4-((3-bromopyridin-2-yl)oxy)piperidine-1-carboxylate (see PREPARATION P20.4; 4 g, 11.2 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.58 g, 12.4 mmol) and Na2CO3 (2.38 g, 22.4 mmol) in 1,4-dioxane (60 mL) and H2O (6 mL) was added Pd(dppf)Cl2 (410 mg, 0.56 mmol) then the reaction mixture was stirred at 110° C. under N2 for overnight. The reaction mixture was filtered through CELITE® and washed with CH2Cl2. The organic layer was concentrated and the crude product was purified by silica gel column to give the desired compound (3.5 g, 8.7 mmol, yield 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08497265B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-34374bb58d824d9895cc0cc90a9145dd
Source note	uspto-grants-2013_07