Potassium Carbonate → Methyl 3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester	HCID 53217136	—
Reactant	HCID 178493805	HCID 178493805	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoate	HCID 90030202	73.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

Into a 50-mL three neck round-bottom flask, purged and maintained with nitrogen, was placed a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (414 mg, 1.50 mmol) in dioxane (6 mL). Potassium carbonate (2 M, 2.5 mL, 5.00 mmol), 3-iodo-4-methoxy-1H-pyrazole (compound 244.5, 224 mg, 1.00 mmol), Pd(dppf)Cl2 (73 mg, 0.10 mmol) were added to the reaction and the resulting mixture was stirred overnight at 90° C. The resulting mixture was cooled, then diluted with EtOAc (80 mL) and washed with brine (2×30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1/1) as eluent to obtain the title compound as a yellow oil (180 mg, 73%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09428502B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-0d5e1597ddb54580b8583828a9914c95
Source note	uspto-grants-2016_08