Dichloromethane → 3-[5-(2,3-Dichloro-phenyl)-pyridin-3-yl]-propionic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2,3-Dichlorobenzeneboronic acid	HCID 2734661	—
Reactant	Methyl 3-(5-bromopyridin-3-yl)propanoate	HCID 59578425	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-[5-(2,3-Dichloro-phenyl)-pyridin-3-yl]-propionic acid methyl ester	HCID 59578405	51.3%

Reaction Steps

A mixture of 3-(5-bromo-pyridin-3-yl)-propionic acid methyl ester (155 mg), 2,3-dichlorobenzeneboronic acid (142 mg, 0.744 mmol), PdCl2(dppf).CH2Cl2 adduct (48.6 mg, 0.059 mmol) and Na2CO3 (2 M, 0.929 ml, 1.859 mmol) in DMF (5 ml) was heated at 100° C. After 40 min, solvent was removed in vacuo. The residue was purified via flash column (EtOAc/Heptane=0-20-25%, v/v) to give 3-[5-(2,3-Dichloro-phenyl)-pyridin-3-yl]-propionic acid methyl ester (101 mg, 0.326 mmol, 43% yield). ESI-MS m/z: 310[M+1]+; 1H NMR (CDCl3, 400 MHz) δ 2.71 (t, J=7.6 Hz, 2H), 3.05 (t, J=7.6 Hz, 2H), 3.70 (s, 3H), 7.23 (dd, J=7.6, 1.6 Hz, 1H), 7.30 (t, J=7.6 Hz, 1H), 7.53 (dd, J=7.6, 1.6 Hz, 1H), 7.63 (s, 1H), 8.52 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08519142B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-516dcbe3d51c4b7f9e4239a50e30e6e2
Source note	uspto-grants-2013_08