Dichloromethane → Methyl 4-methyl-3-(1H-pyrazol-5-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	3-Iodo-1H-pyrazole	HCID 1239830	—
Reactant	5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester	HCID 53217136	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 4-methyl-3-(1H-pyrazol-5-yl)benzoate	HCID 90030661	41.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-1H-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2.DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90° C. for 18 h, then cooled and diluted with EtOAc and filtered through Celite®. The filtrate was washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2; 0-30% EtOAc in hexanes) to yield 258 mg (41%) of the title compound as a solid. m/z (ES+) 217 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09428502B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-261e5117cac04f79963c187fdd4de7bf
Source note	uspto-grants-2016_08