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
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Oxygen | HCID 977 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Bis(2-dicyclohexylphosphinophenyl)ether | HCID 4499096 | — |
| Reactant | 2,6-Difluoro-4-methoxybenzeneboronic acid | HCID 16217424 | — |
| Reactant | 1-(3-Bromo-4-trifluoromethyl-benzoylamino)-4-methyl-cyclohexanecarboxylic acid methyl ester | HCID 67170514 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-[(2',6'-Difluoro-4'-methoxy-6-trifluoromethyl-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic Acid Methyl Ester | HCID 67168800 | 4.6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618304B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-a8a6adb5cb1d48ae8808bd61fdfae16b |
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| Source note | uspto-grants-2013_12 |
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