Water → 6-(1H-Imidazol-2-yl)picolinonitrile

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	2-chloro-6-(1H-imidazol-2-yl)pyridine	HCID 57503313	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Product	6-(1H-Imidazol-2-yl)picolinonitrile	HCID 23208031	—

Reaction Conditions

Temperature	40 °C

Reaction Steps

A mixture of 2-chloro-6-(1H-imidazol-2-yl)-pyridine (800 mg, 4.45 mmol), zinc cyanide (313 mg, 2.68 mmol), Pd2(dba)3 (122 mg, 0.133 mmol), DPPF (144 mg, 0.27 mmol) and water (0.1 mL) in DMF (10 mL) is degassed with argon for 15 minutes. The mixture is then heated at 40° C. overnight in a sealed tube. Solvent is removed and water (30 mL) is added and the mixture is extracted with methylene chloride. On drying (MgSO4), the solvent is removed. Column separation gives the product (172).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07271170B2
Source dataset	uspto-grants-2007_09
ORD ID	ord-fd84e3eaea18487aa78ef074fc16521a
Source note	uspto-grants-2007_09