Sodium Carbonate → methyl 4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Methyl 4-bromofuran-2-carboxylate	HCID 12239443	—
Reactant	1-Ethylpyrazole-5-boronic acid, pinacol ester	HCID 53217252	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	methyl 4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate	HCID 57826888	74.5%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of methyl 4-bromo-2-furancarboxylate (1.0 g, 4.88 mmol) in THF (20 mL) was added aqueous Na2CO3 (2N, 8 mL, 16 mmol.), PdCl2(dppf) (0.35 g, 0.49 mmol) and 1-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.3 g, 5.85 mmol). The reaction mixture was heated to 70° C. in a sealed tube. After 2 h, the reaction mixture was concentrated under vacuum and purified on silica (EtOAc/Hex, 20-40%) to afford the title compound (0.8 g, 74.5%) as a light yellow solid: LC-MS (ES) m/z=221 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946278B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-c5c31afa9ec643fa913915c48669c0ba
Source note	uspto-grants-2015_02