Sodium Carbonate → Methyl 4-(6-methoxyquinolin-2-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Chloro-6-methoxyquinoline	HCID 83647	—
Reactant	4-Methoxycarbonylphenylboronic acid	HCID 2734369	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	Methyl 4-(6-methoxyquinolin-2-yl)benzoate	HCID 66980098	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 2-chloro-6-methoxyquinoline (see U.S. 61/391,225 for synthesis) (200 mg, 1.0 mmol), 4-(methoxycarbonyl) phenylboronic acid (205 mg, 1.1 mmol), Pd(dppf)Cl2 (366 mg, 0.5 mmol) and sodium carbonate (212 mg, 2.0 mmol) in 1,4-dioxane/water (3 mL/0.6 mL) was heated to 120° C. by microwave for 1 h. The precipitates were filtered; washed with EtOAc (10 mL), acetone (10 mL) and water (10 mL) separately; dried to give the product as a black solid. (120 mg, 40.9%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09433618B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-0c6c5bb0a5c943cab6c7cb134fb85ce2
Source note	uspto-grants-2016_09