Water → 3-[3-(2-Hydroxy-phenyl)-pyrazin-2-YL]-azetidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	(2-Hydroxyphenyl)boronic acid	HCID 2773454	—
Reactant	Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate	HCID 59351411	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-[3-(2-Hydroxy-phenyl)-pyrazin-2-YL]-azetidine-1-carboxylic acid tert-butyl ester	HCID 136123733	92%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (540 mg, 2.0 mmol, see Preparation 2), 2-hydroxy-phenylboronic acid (71) (303.6 mg, 2.2 mmol), K3PO4 (818 mg, 4.0 mmol), in dioxane (20 mL) and water (4 mL) was added Pd(dppf)Cl2 (73.2 mg, 0.1 mmol) then the reaction mixture was stirred at 90° C. under nitrogen atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give (72) (601.7 mg, 1.84 mmol, yield 91.85%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08957073B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-23a5ed2311e14cd1ad14bbf0c19a1106
Source note	uspto-grants-2015_02