Dichloromethane → 2-Chloro-4-[5-chloro-4-(1-hydroxy-ethyl)-pyridin-3-yl]-benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile	HCID 57926113	—
Reactant	1-(3-Bromo-5-chloro-pyridin-4-yl)-ethanol	HCID 67155021	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Chloro-4-[5-chloro-4-(1-hydroxy-ethyl)-pyridin-3-yl]-benzonitrile	HCID 71104925	33%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To the solution of 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (412 mg, 1.56 mmol), 1-(3-Bromo-5-chloro-pyridin-4-yl)-ethanol (370 mg, 1.56 mmol) and PdCl2(dppf). CH2Cl2 adduct (64 mg, 0.08 mmol) in DMF (10 mL) was added 2M Na2CO3 solution (2.35 ml, 4.70 mmol) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4Cl solution. After extraction with DCM and separation, the combined extracts were concentrated and purified by ISCO 12 g (0-30%, EtOAc/Heptane, v/v) to give 2-Chloro-4-[5-chloro-4-(1-hydroxy-ethyl)-pyridin-3-yl]-benzonitrile (150 mg, 33%) as colorless solid; ESI-MS m/z: 293 [M+H]+,

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08519134B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-206d2d1822484f35ad64ad584e98475d
Source note	uspto-grants-2013_08