Sodium Carbonate → 4-(7-Methoxyquinolin-3-yl)benzoic acid

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Carboxyphenylboronic Acid	HCID 312183	—
Reactant	3-Bromo-7-methoxyquinoline	HCID 18788548	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethoxyethane ethanol water	HCID 86587095	—
Product	4-(7-Methoxyquinolin-3-yl)benzoic acid	HCID 67974668	29.1%

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a mixture of 3-bromo-7-methoxyquinoline (Intermediate 13, 380 mg, 1.6 mmol), 4-boronobenzoic acid (266 mg, 1.6 mmol) and Na2CO3 (848 mg, 8.0 mmol) in DME/H2O/EtOH (5 mL, V/V/V=1/1/0.5) was added Pd(dppf)Cl2 (585 mg, 0.8 mmol). The mixture was heated to 120° C. by microwave for 1 h. The mixture was partitioned between water (20 mL) and ethyl acetate (20 mL). The aqueous phase was separated and acidified to pH=3 with 1 N HCl. The precipitate was filtered and dried in vacuo to afford product as a powder (130 mg, 29.1%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09221810B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-83c68a3298034eb8a7ce3fa9f0b674a6
Source note	uspto-grants-2015_12