Water → (1-Methyl-1H-benzoimidazol-2-YL)-[3-(3-phenyl-pyrazin-2-YL)-azetidin-1-YL]-methanone

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	HCID 58546825	HCID 58546825	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(1-Methyl-1H-benzoimidazol-2-YL)-[3-(3-phenyl-pyrazin-2-YL)-azetidin-1-YL]-methanone	HCID 58546740	70%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a stirred solution of [3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-(1-methyl-1H-benzoimidazol-2-yl)-methanone (100 mg, 0.30 mmol) in dioxane (10 mL) was added phenylboronic acid (87 mg, 0.71 mmol), Na2CO3 (152 mg, 1.4 mmol) and H2O (2 mL). The reaction mixture was degassed with N2 and then PdCl2(dppf) (35 mg, 0.05 mmol) was added. The reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was left to reach RT and filtered through a pad of CELITE® and the filter cake was washed with CH2Cl2 (20 mL×3). The combined filtrates were evaporated in vacuo and the residue was purified by column chromatography to give the desired compound (60 mg, 0.17 mmol, yield 70%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08957073B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-d88ad0087c894acb9ea3ccff4c228d80
Source note	uspto-grants-2015_02