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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 58065Generated: October 25, 2026

[4-(Methoxycarbonyl)-2-methylphenyl]boronic acid → methyl 3-methyl-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoate

https://huagongshe.com/reaction/58065

Reaction equation

Participants

RoleNameHCIDCharge
Reactant[4-(Methoxycarbonyl)-2-methylphenyl]boronic acidHCID 22171419—
Reactant4-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 24729232—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
Solvent1,4-DioxaneHCID 31275—
SolventSodium BicarbonateHCID 516892—
Productmethyl 3-methyl-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoateHCID 89782937—

Reaction Conditions

Temperature140 °C

Reaction Steps

To a microwave vial was added a mixture 4-bromo-6-(trifluoromethyl)-1H-indazole (0.478 g, 1.804 mmol), (4-(methoxycarbonyl)-2-methylphenyl)boronic acid (0.35 g, 1.804 mmol) and PdCl2(dppf) (0.066 g, 0.090 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the residue was diluted with EtOAc and washed with water. The volatiles were removed via rotary evaporation to give the title compound, which was used without further purification (0.53 g). ESI-MS m/z [M+H]+ calc'd for C17H13F3N2O2, 335.1. found 335.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434743B2
Source datasetuspto-grants-2016_09
ORD IDord-baa272f5ec214d7b956cc5f094773292
Source noteuspto-grants-2016_09