Potassium Carbonate → methyl 3-(1-methyl-1H-pyrazol-5-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	3-(Methoxycarbonyl)benzeneboronic acid	HCID 2734714	—
Reactant	5-Bromo-1-methyl-1H-pyrazole	HCID 17933381	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	methyl 3-(1-methyl-1H-pyrazol-5-yl)benzoate	HCID 69687203	83.6%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (270 mg, 1.5 mmol), 5-bromo-1-methyl-1H-pyrazole (200 mg, 1.25 mmol), K2CO3 (518 mg, 3.75 mmol) and Pd(dppf)Cl2 (10 mg) in a mixture solution of dioxane (8 mL) and H2O (2 mL) was stirred at 120° C. for 30 min under microwave heating. The catalyst was filtered and the filtrate concentrated. The residue was then purified by column chromatography to give provide the desired product as a colorless oil (226 mg, Yield 60%). It was used directly in the next step. LCMS (m/z): 217.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993555B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-cb86823d64734996bcf4975768bfc11b
Source note	uspto-grants-2015_03