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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1918362Generated: November 1, 2026

Oxygen → 1-[(2',6'-Difluoro-4'-methoxy-6-trifluoromethyl-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic Acid Methyl Ester

https://huagongshe.com/reaction/1918362

Reaction equation

Participants

RoleNameHCIDCharge
ReactantOxygenHCID 977—
ReactantPotassium Phosphate, TribasicHCID 62657—
ReactantBis(2-dicyclohexylphosphinophenyl)etherHCID 4499096—
Reactant2,6-Difluoro-4-methoxybenzeneboronic acidHCID 16217424—
Reactant1-(3-Bromo-4-trifluoromethyl-benzoylamino)-4-methyl-cyclohexanecarboxylic acid methyl esterHCID 67170514—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product1-[(2',6'-Difluoro-4'-methoxy-6-trifluoromethyl-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic Acid Methyl EsterHCID 671688004.6%

Reaction Steps

300 mg of 1-(3-Bromo-4-trifluoromethyl-benzoylamino)-4-methyl-cyclohexanecarboxylic acid methyl ester, 267 mg of 2,6-difluoro-4-methoxyphenylboronic acid, 65 mg of tris(dibenzylideneacetone)di-palladium(0), 96 mg of bis(2-dicyclohexylphosphinophenyl)ether, 453 mg of K3PO4, and 1 g of molecular sieve 4 Å were added to 10 ml of toluene. The mixture was made oxygen-free by passing argon through it. Then, the mixture was kept at 160° C. under microwave irradiation for 2 h. Then, 267 mg of 2,6-difluoro-4-methoxyphenylboronic acid, 65 mg of tris(dibenzylideneacetone)di-palladium(0), 96 mg of bis(2-dicyclohexylphosphinophenyl)ether were added and the mixture was kept at 160° C. under microwave irradiation for 2 h. The mixture was cooled to room temperature and 100 ml of EA added. The mixture was then washed twice using 20 ml of a saturated aqueous Na2CO3-solution each. The organic layer was dried using MgSO4 and the solvent evaporated. Chromatography on silica gel using EA/HEP 1:5 yielded 16 mg of the title compound, viscous oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618304B2
Source datasetuspto-grants-2013_12
ORD IDord-a8a6adb5cb1d48ae8808bd61fdfae16b
Source noteuspto-grants-2013_12