Sodium Carbonate → Methyl 6-(6-hydroxynaphthalen-2-yl)nicotinate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(6-Hydroxynaphthalen-2-yl)boronic acid	HCID 4349738	—
Reactant	Methyl 6-bromopyridine-3-carboxylate	HCID 13349623	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	Methyl 6-(6-hydroxynaphthalen-2-yl)nicotinate	HCID 136331263	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 6-hydroxynaphthalen-2-ylboronic acid (250 mg, 1.33 mmol), methyl 6-bromonicotinate (260 mg, 1.21 mmol), Pd(dppf)Cl2 (90 mg, 0.12 mmol) and sodium carbonate (205 mg, 2.41 mmol) in DME/water (3 mL/1 mL) was heated to 120° C. by microwave for 1 h. Then the mixture was partitioned with water (10 mL) and EA (20 mL). The precipitate was filtered off. The organic phase was separated, washed with brine (15 mL), dried over Na2SO4 and concentrated to afford product (crude, 380 mg) as a brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249132B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-3c534e60dcc64abb98b11ca9c1b020cb
Source note	uspto-grants-2016_02