Potassium Carbonate → HCID 178509515, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	HCID 178509517	HCID 178509517	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	HCID 178509515	HCID 178509515	19.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

The mixture of 2-[1-(3-chloro-pyrazin-2-yl)-piperidin-4-yl]-1H-benzoimidazole-5-carbonitrile (160 mg, 0.47 mol), phenylboronic acid (69.3 mg, 0.57 mmol), K2CO3 (131 mg, 0.95 mmol) and Pd(dppf)Cl2 (34 mg, 0.047 mmol) in toluene (10 mL) and H2O (3 mL) was stirred at 90° C. under N2 for 12 h. Then it was poured into H2O and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give the crude product which was purified by column (ethyl acetate:petroleum ether=1:2) to give the compound 2-[1-(3-phenyl-pyrazin-2-yl)-piperidin-4-yl]-1H-benzoimidazole-5-carbonitrile (35 mg, yield 19.1%) as white solid. [M+1] 381. IC50 (uM) 0.272.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946230B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-a000803f67d94972a386bb1f51c57a82
Source note	uspto-grants-2015_02