Dichloromethane → 6-Phenyl-3-pyridineacetonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	2-(6-Chloropyridin-3-yl)acetonitrile	HCID 1475128	—
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	6-Phenyl-3-pyridineacetonitrile	HCID 66980183	—

Reaction Conditions

Temperature	75 °C

Reaction Steps

Phenylboronic acid (4630.9 mg, 37.98 mmol), K3PO4 (20129 mg, 94.95 mmol), and PdCl2(dppf).CH2Cl2 (1291 mg, 1.58 mmol) was added to a solution of 2-(6-chloropyridin-3-yl)acetonitrile (5000 mg, 31.65 mmol) in dioxane (100 mL) and H2O (10 mL). The resulting mixture was stirred at 75° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 2-(6-phenylpyridin-3-yl)acetonitrile: LCMS tR=1.15 Min (5 min run, UV254nm), Mass calculated for, M+194.0, observed LC/MS m/z 195.0 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927562B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-f0f22dba7aa94d72b58f9ad7f03e8670
Source note	uspto-grants-2015_01